1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl ester

Base Information

• Chemical Name: 1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl ester
• CAS No.: 37813-30-2
• Molecular Formula: C12H21NO5
• Molecular Weight: 259.29900
• Hs Code.: 2933990090
• Mol file: 37813-30-2.mol

Synonyms:N-(tert-butoxycarbonyl)-4-hydroxy-L-proline ethyl ester;(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-ethyl ester;1-tert-butyl 2-ethyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;1-Boc-L-hydroxyproline ethyl ester;1-Boc-4-Hydroxy-L-Proline Ethyl Ester;(2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester;(2S,4R)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl-4-hydroxypyrrolidine;(2S,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid-1-tert-butyl ester-2-ethyl ester;(2S,4R)-1-BOC-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER;Boc-L-Hydroxy-Proline Ethyl Ester;

Chemical Property of 1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl ester

Chemical Property:

• Boiling Point: 350.2±42.0 °C(Predicted)
• PKA: 14.30±0.40(Predicted)
• PSA: 76.07000
• Density: 1.189±0.06 g/cm3(Predicted)
• LogP: 0.85770
• Storage Temp.: 2-8°C

Purity/Quality:

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

(2S,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl ester

There total 15 articles about 1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) → (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (37813-30-2)

Guidance literature:

With triethylamine; In ethanol; dichloromethane; at 0 - 20 ℃; for 16.25h;

Reference yield: 100.0%

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (41840-28-2) + (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester (61478-25-9) → (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (37813-30-2)

Guidance literature:

In water; N,N-dimethyl-formamide; at 50 ℃; for 2h;

DOI:10.1021/jo01311a036

Reference yield: 96.0%

ethanol (64-17-5) + di-tert-butyl dicarbonate (24424-99-5) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (37813-30-2)

Guidance literature:

ethanol; 4R-4-hydroxyproline; With thionyl chloride; for 16h; Heating;

di-tert-butyl dicarbonate; With triethylamine; In dichloromethane; for 17h;

DOI:10.1021/jo0490043

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

trans-4-hydroxy-L-proline ethyl ester hydrochloride

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester

Downstream raw materials:

(2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

(2S,4R)-4-benzyloxy-2-methoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl (2S,4R)-4-(benzyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Refernces

• 1、 -. "TYK2 INHIBITORS AND USES THEREOF". Paragraph 00954-00955. . Retrieved 2017/03/21.
• 2、 Gajare, Vikas S.,Khobare, Sandip R.,Malavika,Rajana, Nagaraju,Venkateswara Rao,Syam Kumar. "A short diastereoselective synthesis of cis-(2S,4S) and cis-(2R,4R)-4-hydroxyprolines". supporting information. p. 3743 - 3746. Retrieved 2015/06/08.