1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, 2-methyl 1-(phenylmethyl) ester, (2S,4S)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, 2-methyl 1-(phenylmethyl) ester, (2S,4S)-
• CAS No.: 168263-80-7
• Molecular Formula: C19H26N2O6
• Molecular Weight: 378.42000
• Mol file: 168263-80-7.mol

Synonyms:

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, 2-methyl 1-(phenylmethyl) ester, (2S,4S)-

Chemical Property:

• PSA: 94.17000
• LogP: 2.79260

Purity/Quality:

97% ^*data from raw suppliers

1-benzyl2-methyl(2S,4S)-4-{[(tert-butoxy)carbonyl]amino}pyrrolidine-1,2-dicarboxylate 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, 2-methyl 1-(phenylmethyl) ester, (2S,4S)-

There total 10 articles about 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, 2-methyl 1-(phenylmethyl) ester, (2S,4S)- 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + 4(S)-azido-N-<(phenylmethoxy)carbonyl>-(S)-proline methyl ester (113490-74-7) → methyl (2S,4S)-1-benzyloxycarbonyl-4-tert-butoxycarbonylaminopyrrolidine-2-carboxylate (168263-80-7)

Guidance literature:

With hydrogen; nickel; In ethyl acetate;

DOI:10.1039/b308581c

Reference yield:

(2S,4S)-methyl 4-(tert-butoxycarbonylamino)pyrrolidine-2-carboxylate (168263-82-9,1279200-56-4) + benzyl chloroformate (501-53-1,94274-21-2) → methyl (2S,4S)-1-benzyloxycarbonyl-4-tert-butoxycarbonylaminopyrrolidine-2-carboxylate (168263-80-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → methyl (2S,4S)-1-benzyloxycarbonyl-4-tert-butoxycarbonylaminopyrrolidine-2-carboxylate (168263-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / pyridine

2: 96 percent / NaN₃ / dimethylformamide

3: 95 percent / H₂; Ni / ethyl acetate

With pyridine; sodium azide; hydrogen; nickel; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/b308581c

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

(2S,4S)-1-benzyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

di-tert-butyl dicarbonate

4(S)-azido-N-<(phenylmethoxy)carbonyl>-(S)-proline methyl ester

Downstream raw materials:

4-N-tert-butyloxycarbonylamino-N-benzyloxycarbonyl-L-cis-proline

carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester

{(2S,4S)-4-t-butoxycarbonylamino-1-[(thymin-1-yl)methylcarbonyl]-pyrrolidin-2-yl}methyl 4-nitrophenyl carbonate

{1-[2-((2S,4S)-4-tert-Butoxycarbonylamino-2-hydroxymethyl-pyrrolidin-1-yl)-2-oxo-ethyl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid benzyl ester