((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester

Base Information

• Chemical Name: ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester
• CAS No.: 681293-19-6
• Molecular Formula: C₂₆H₃₆N₄O₈S
• Molecular Weight: 564.66

Synonyms:((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester

Chemical Property of ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester

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Technology Process of ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester

There total 8 articles about ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl 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:

(4aS,7R,7aR)-7-Hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindine-4-carboxylic acid amide + ((1S,2S)-1-Chlorocarbonylmethanesulfonylaminocarbonyl-2-methyl-butyl)-carbamic acid benzyl ester → ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aS,7R,7aR)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester (681293-20-9) + ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester (681293-19-6)

Guidance literature:

(4aS,7R,7aR)-7-Hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindine-4-carboxylic acid amide; ((1S,2S)-1-Chlorocarbonylmethanesulfonylaminocarbonyl-2-methyl-butyl)-carbamic acid benzyl ester; With dmap; triethylamine; In N,N-dimethyl-formamide; at 0 - 18 ℃; for 1.5h;

With hydrogen; 10percent Pd/C; In methanol; at 18 ℃; for 4h; under 760.051 Torr; Further stages. Title compound not separated from byproducts.;

DOI:10.1039/b104890m

Reference yield:

(4aR,7S,7aS)-7-Hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindine-4-carboxylic acid amide + ((1S,2S)-1-Chlorocarbonylmethanesulfonylaminocarbonyl-2-methyl-butyl)-carbamic acid benzyl ester → ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester (681293-19-6)

Guidance literature:

With N,N-dimethyl-formamide; In dichloromethane; at 0 ℃;

DOI:10.1016/S0968-0896(03)00237-2

Reference yield:

((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (405096-74-4) → ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester (681293-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: DMF / CH₂Cl₂ / 0 °C

With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1016/S0968-0896(03)00237-2

upstream raw materials:

N-Cbz-L-Isoleucine

((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid

cyclopent-2-enone

2-(hydroxymethyl)cyclopent-2-enone

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