(L)-2-DIAZOACETYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Base Information

• Chemical Name: (L)-2-DIAZOACETYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• CAS No.: 101130-03-4
• Molecular Formula: C₁₁H₁₇N₃O₃
• Molecular Weight: 239.274
• Hs Code.: 2933990090
• Mol file: 101130-03-4.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 2-(diazoacetyl)-, 1,1-dimethylethyl ester, (2S)- (9CI);1-Pyrrolidinecarboxylic acid, 2-(diazoacetyl)-, 1,1-dimethylethyl ester, (S)-

Chemical Property of (L)-2-DIAZOACETYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Chemical Property:

• Melting Point: 45-46 °C
• PSA: 84.00000
• LogP: 1.27456

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (L)-2-DIAZOACETYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

There total 14 articles about (L)-2-DIAZOACETYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 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: 86.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate (101130-03-4)

Guidance literature:

1-(tert-butoxycarbonyl)-L-proline; With pyridine; dmap; di-tert-butyl dicarbonate; In tetrahydrofuran; at 0 ℃;

diazomethane; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1039/b204652k

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + isobutyl chloroformate (543-27-1) → tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate (101130-03-4)

Guidance literature:

1-(tert-butoxycarbonyl)-L-proline; isobutyl chloroformate; With 4-methyl-morpholine; In dichloromethane; at -25 ℃; for 0.333333h; Inert atmosphere;

diazomethane; In diethyl ether; dichloromethane; at -25 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.09.136

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + chloroformic acid ethyl ester (541-41-3) → tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate (101130-03-4)

Guidance literature:

With sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; water; toluene;

upstream raw materials:

diazomethane

1-(tert-butoxycarbonyl)-L-proline

N-Boc-(S)-proline chloride

(S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(2S)-tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-2-carboxylate

tert-butyl (S)-2-[2-(benzyloxy)-2-oxoethyl]pyrrolidine-1-carboxylate

[(2S)-pyrrolidin-2-yl]acetic acid methyl ester

Boc-(S)-β³-HPro-(R)-β³-HPro-OBn

Refernces

• 1、 Vasanthakumar, Ganga-Ramu,Patil, Basanagoud S.,Suresh Babu, Vommina V.. "Homologation of α-amino acids to β-amino acids using Boc2O". . p. 2087 - 2089. Retrieved 2002.
• 2、 Hanessian, Stephen,Chattopadhyay, Amit Kumar. "Iminium ion-enamine cascade cyclizations: Facile access to structurally diverse azacyclic compounds and natural products". supporting information. p. 232 - 235. Retrieved 2014/01/23.
• 3、 Vishwanathaa,Narendra,Sureshbabu, Vommina V.. "CuI-promoted one-pot synthesis of N-boc protected β-ketotriazole amino acids: Application in the synthesis of new class of dipeptidomimetics". experimental part. p. 308 - 314. Retrieved 2012/07/17.