methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

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Chemical Name:methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate
CAS No.:874163-03-8
Molecular Formula:C₂₅H₃₄N₄O₈
Molecular Weight:518.567
Hs Code.:

Synonyms:methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

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Chemical Property of methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

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Technology Process of methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

There total 5 articles about methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate 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: 60.0%

: 874163-00-5
(2S,4R)-1-(tert-butoxycarbonyl)-4-(N-benzyloxycarbonyl)aminoproline

: 3(R)-2-oxo-1-pyrrolidineacetic acid methyl ester trifluoroacetate

: 874163-03-8
methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

Guidance literature:: (2S,4R)-1-(tert-butoxycarbonyl)-4-(N-benzyloxycarbonyl)aminoproline; With N-methylcyclohexylamine; isobutyl chloroformate; In tetrahydrofuran; at -23 ℃; for 0.166667h;

With benzotriazol-1-ol; In tetrahydrofuran; at -23 ℃; for 0.333333h;

3(R)-2-oxo-1-pyrrolidineacetic acid methyl ester trifluoroacetate; With N-methylcyclohexylamine; In tetrahydrofuran; at 20 ℃; for 96h;
DOI:10.1021/jm050644n

Reference yield:

: 874162-95-5
(2S,4S)-1-(tert-butoxycarbonyl)-4-bromoproline benzyl ester

: 874163-03-8
methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / NaN₃ / dimethylformamide / 55 °C

2.1: 95 percent / H₂ / Pd/C / ethanol; H₂O / 28 h / 3878.61 Torr

3.1: 63 percent / aq. NaOH / 0 - 20 °C

4.1: N-methylpiperidine; isobutylchloroformate / tetrahydrofuran / 0.17 h / -23 °C

4.2: HOBt / tetrahydrofuran / 0.33 h / -23 °C

4.3: 60 percent / N-methylpiperidine / tetrahydrofuran / 96 h / 20 °C

With N-methylcyclohexylamine; sodium hydroxide; sodium azide; hydrogen; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jm050644n

Reference yield:

: 89813-47-8
N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

: 874163-03-8
methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 82 percent / CBr₄; 1,2-bis(diphenylphosphino)ethane / tetrahydrofuran / 20 h / 20 °C

2.1: 99 percent / NaN₃ / dimethylformamide / 55 °C

3.1: 95 percent / H₂ / Pd/C / ethanol; H₂O / 28 h / 3878.61 Torr

4.1: 63 percent / aq. NaOH / 0 - 20 °C

5.1: N-methylpiperidine; isobutylchloroformate / tetrahydrofuran / 0.17 h / -23 °C

5.2: HOBt / tetrahydrofuran / 0.33 h / -23 °C

5.3: 60 percent / N-methylpiperidine / tetrahydrofuran / 96 h / 20 °C

With N-methylcyclohexylamine; sodium hydroxide; sodium azide; carbon tetrabromide; hydrogen; 1,2-bis-(diphenylphosphino)ethane; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jm050644n