Boc-L-beta-homoproline

Base Information

• Chemical Name: Boc-L-beta-homoproline
• CAS No.: 56502-01-3
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID40350915
• Nikkaji Number: J1.216.151D
• Wikidata: Q72449518
• Mol file: 56502-01-3.mol

Synonyms:56502-01-3;Boc-L-beta-homoproline;(S)-2-(1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)acetic acid;(S)-2-(1-Boc-2-pyrrolidinyl)acetic acid;MFCD01862939;2-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]acetic acid;2-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-yl]acetic acid;2-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]acetic acid;Boc-|A-HoPro-OH;[(2s)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]acetic acid;Boc-betaPro-OH;Boc-I(2)-HoPro-OH;Boc-Pro-(C#CH2)OH;SCHEMBL115846;DTXSID40350915;AMY19036;CS-M1624;AKOS015908581;AC-4224;DS-15932;(S)-2-(1-Boc-2-pyrrolidinyl)aceticacid;(S)-2-(Carboxymethyl)pyrrolidinium chloride;Boc-beta3-Homopro-OH, >=98.0% (TLC);(S)-2-(1-BOC-pyrrolidin-2-yl)acetic acid;EN300-816474;AU-004/43509869;[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]acetic acid;W-203129;[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]acetic acid;1-(tert-Butyloxycarbonyl)pyrrolidine-2alpha-acetic acid;(S)-1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINEACETIC ACID;(S)-2-carboxymethyl-pyrrolidine-1-carboxylic acid tert butyl ester;(s)-2-carboxymethylpyrrolidine-1-carboxylic acid tert-butyl ester;2-(S)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester;((2s)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-2-pyrrolidinyl)acetic acid;(S)-2-CARBOXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;[(2S)-1-{[(2-Methyl-2-propanyl)oxy]carbonyl}-2-pyrrolidinyl]acetic acid

Chemical Property of Boc-L-beta-homoproline

Chemical Property:

• Vapor Pressure: 4.5E-06mmHg at 25°C
• Melting Point: ~165°C (dec.)(lit.)
• Refractive Index: 1.491
• Boiling Point: 357.4 °C at 760 mmHg
• PKA: 4.56±0.10(Predicted)
• Flash Point: 169.9 °C
• PSA: 66.84000
• Density: 1.151g/cm³
• LogP: 1.79850
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 229.13140809
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-L-β-homoproline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1CC(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1CC(=O)O
• Uses: Building block for necine alkaloids. Boc-L-beta-homoproline is an amino acid derivative which is a reagent in the synthesis of dihydroisoxazole inhbitors of human transglutaminase 2, an enzyme that catalyzes the modification of glutamine residues. This enzyme has been implicated in numerous inflmmatory, fibrotic and other diseases.

Technology Process of Boc-L-beta-homoproline

There total 2 articles about Boc-L-beta-homoproline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tert-butyl 2-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate (118758-56-8) → (2S)-1-tert-butoxycarbonyl-2-carboxymethylpyrrolidine (56502-01-3) + 2-(R)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (101555-60-6) + 2-ethoxycarbonylmethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

With Burkholderia cepacia lipase; hydrogenchloride; In tetrahydrofuran; phosphate buffer; at 25 ℃; for 48h; pH=7;

DOI:10.1016/j.tetasy.2004.09.022

Reference yield:

2-methoxycarbonylmethylpyrrolidine-1-carboxylic acid tert-butyl ester (813433-68-0) → (2S)-1-tert-butoxycarbonyl-2-carboxymethylpyrrolidine (56502-01-3) + methyl (R)-2-[N(1')-(tert-butoxycarbonyl)pyrrolidin-2'-yl]ethanoate (132482-05-4,813433-68-0)

Guidance literature:

With Burkholderia cepacia lipase; hydrogenchloride; In tetrahydrofuran; phosphate buffer; at 25 ℃; for 30h; pH=7;

DOI:10.1016/j.tetasy.2004.09.022

Reference yield: 97.0%

H-Thr-OBzl p-toluenesulphonate (63566-02-9) + (2S)-1-tert-butoxycarbonyl-2-carboxymethylpyrrolidine (56502-01-3) → Boc-homo-Pro-Thr-OBzl (158396-78-2)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

upstream raw materials:

tert-butyl 2-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

2-methoxycarbonylmethylpyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

Boc-homo-Pro-Thr-OBzl

(S)-2-{[2-(2-tert-Butoxycarbonylsulfanyl-ethylsulfanyl)-4-(tert-butyl-dimethyl-silanyloxy)-phenylcarbamoyl]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-2-{[4-Benzyloxy-2-(2-tert-butoxycarbonylsulfanyl-ethylsulfanyl)-phenylcarbamoyl]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S)-tert-butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylate

Refernces