1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4R)-

Base Information

Chemical Name:1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4R)-
CAS No.:874163-10-7
Molecular Formula:C23H30N8O7
Molecular Weight:530.541
Hs Code.:

1-Pyrrolidinecarboxylic acid,
2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[
(4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4R)-

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Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4R)-

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Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4R)-

There total 9 articles about 1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4R)- 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: 62.0%

: 3(R)-[(4(R)-(4-amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

: 96602-46-9
succinimide 4-azidosalicylate

: 874163-10-7
3(R)-[(4(R)-((4-azido-2-hydroxybenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

Guidance literature:: In acetonitrile; for 18h; Heating;
DOI:10.1021/jm050644n

Reference yield:

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

: 874163-10-7
3(R)-[(4(R)-((4-azido-2-hydroxybenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

Guidance literature:: Multi-step reaction with 7 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

5.1: 92 percent / NH₃ / methanol / 20 h / 20 °C

6.1: H₂ / Pd/C / methanol / 24 h / 2585.74 Torr

7.1: 62 percent / acetonitrile / 18 h / Heating

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

Reference yield:

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

: 874163-10-7
3(R)-[(4(R)-((4-azido-2-hydroxybenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

Guidance literature:: Multi-step reaction with 4 steps

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

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

1.3: 60 percent / N-methylpiperidine / tetrahydrofuran / 96 h / 20 °C

2.1: 92 percent / NH₃ / methanol / 20 h / 20 °C

3.1: H₂ / Pd/C / methanol / 24 h / 2585.74 Torr

4.1: 62 percent / acetonitrile / 18 h / Heating

With N-methylcyclohexylamine; ammonia; hydrogen; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1021/jm050644n