(4S)-1-[(2S,3S)-3-(N₂-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide

Base Information

• Chemical Name: (4S)-1-[(2S,3S)-3-(N₂-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide
• CAS No.: 166382-65-6
• Molecular Formula: C₃₁H₄₀ClN₅O₇
• Molecular Weight: 630.141

Synonyms:(4S)-1-[(2S,3S)-3-(N₂-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide

Chemical Property of (4S)-1-[(2S,3S)-3-(N₂-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide

Chemical Property:

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Technology Process of (4S)-1-[(2S,3S)-3-(N₂-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide

There total 6 articles about (4S)-1-[(2S,3S)-3-(N₂-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide 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:

(4S)-N-t-butyl-4-chloro-L-prolinamide hydrochloride (166383-85-3) + diethyl cyanophosphonate (2942-58-7) + Z-Asn-(2S,3S)-AHPBA-OH (143978-10-3) → (4S)-1-[(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide (166382-65-6)

Guidance literature:

With sodium chloride; sodium hydrogencarbonate; triethylamine; citric acid; In N-methyl-acetamide; methanol; dichloromethane;

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (4S)-1-[(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide (166382-65-6)

Guidance literature:

Multi-step reaction with 5 steps

1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -10 °C

2: tetrahydrofuran / 24 h / -5 - 0 °C

3: 89 percent / CCl₄, Ph₃P / 2 h / Heating

4: HCl / dioxane / 0.5 h / Ambient temperature

5: DEPC, Et₃N / dimethylformamide / 3 h

With 4-methyl-morpholine; hydrogenchloride; tetrachloromethane; triethylamine; triphenylphosphine; diethyl dicarbonate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/0968-0896(96)00130-7

Reference yield:

1-tert-butoxycarbonyl-4(R)-hydroxy-L-proline tert-butylamide (143978-73-8) → (4S)-1-[(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-4-chloro-L-prolinamide (166382-65-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / CCl₄, Ph₃P / 2 h / Heating

2: HCl / dioxane / 0.5 h / Ambient temperature

3: DEPC, Et₃N / dimethylformamide / 3 h

With hydrogenchloride; tetrachloromethane; triethylamine; triphenylphosphine; diethyl dicarbonate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/0968-0896(96)00130-7

upstream raw materials:

Z-Asn-(2S,3S)-AHPBA-OH

4(S)-Cl-Pro-tert-butylamide

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

1-tert-butoxycarbonyl-4(R)-hydroxy-L-proline tert-butylamide

Downstream raw materials:

(S)-2-Amino-N¹-[(1S,2S)-1-benzyl-3-((2S,4S)-2-tert-butylcarbamoyl-4-chloro-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-succinamide

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