(2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:859235-94-2
Molecular Formula:C₂₇H₃₉N₃O₇
Molecular Weight:517.623
Hs Code.:

(2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:(2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 14 articles about (2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-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: 73.0%

: 859235-93-1
(2S,4R)-2-{[(1R,2R)-2-Methoxycarbonyl-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 859235-94-2
(2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With tetra(n-butyl)ammonium hydroxide; In tetrahydrofuran; at 0 ℃; for 0.75h;
DOI:10.1002/chem.200400977

Reference yield:

: (2R,3R)-2-Amino-3-(benzyloxycarbonyl-methyl-amino)-butyric acid methyl ester

: 859235-94-2
(2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 0.135 g / tetrahydrofuran / 24 h / 20 °C

2: 100 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3: 0.135 g / 2,4,6-trimethylpyridine; 7-aza-1-hydroxybenzotriazole / ethyl acetate / 15 h / 20 °C

4: aq. HCl / ethyl acetate / 3 h / 20 °C

5: 0.122 g / 2,4,6-trimethylpyridine; i-Pr₂NEt / acetonitrile / 16 h / 20 °C

6: Et₂NH / acetonitrile / 0.67 h / 20 °C

7: 0.104 mg / N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride; 7-aza-1-hydroxybenzotriazole; 2,4,6-trimethylpyridine / CH₂Cl₂ / 16 h / 20 °C

8: 73 percent / aq. tetra-n-butylammonium hydroxide / tetrahydrofuran / 0.75 h / 0 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; tetra(n-butyl)ammonium hydroxide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1002/chem.200400977

Reference yield:

: 859235-83-9
methyl (2S,3R)-3-(benzyloxycarbonyl-N-methylamino)-2-hydroxybutyrate

: 859235-94-2
(2S,4R)-2-{[(1R,2R)-2-Carboxy-1-methyl-2-(4-methyl-benzyloxycarbonylamino)-ethyl]-methyl-carbamoyl}-4-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: Et₃N / CH₂Cl₂ / 5 h / -30 - 20 °C

2: 0.191 g / NaN₃ / dimethylformamide / 15 h / 70 °C

3: PPh₃; H₂O / tetrahydrofuran / 24 h / 20 °C

4: 0.135 g / tetrahydrofuran / 24 h / 20 °C

5: 100 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

6: 0.135 g / 2,4,6-trimethylpyridine; 7-aza-1-hydroxybenzotriazole / ethyl acetate / 15 h / 20 °C

7: aq. HCl / ethyl acetate / 3 h / 20 °C

8: 0.122 g / 2,4,6-trimethylpyridine; i-Pr₂NEt / acetonitrile / 16 h / 20 °C

9: Et₂NH / acetonitrile / 0.67 h / 20 °C

10: 0.104 mg / N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride; 7-aza-1-hydroxybenzotriazole; 2,4,6-trimethylpyridine / CH₂Cl₂ / 16 h / 20 °C

11: 73 percent / aq. tetra-n-butylammonium hydroxide / tetrahydrofuran / 0.75 h / 0 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride; sodium azide; 1-hydroxy-7-aza-benzotriazole; tetra(n-butyl)ammonium hydroxide; water; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.200400977