Diisopropylethylamine → (S)-2-{4'-[(5-chloro-4-isopropoxy-3-methyl-benzofuran-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester

HRID 29381Notes

Reaction equation

HRID 29381 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[C:7]([CH3:13])[C:6]=2[C:14]=1[O:15][CH:16]([CH3:18])[CH3:17].[C:19]([O:23][C:24](=[O:46])[C@@H:25]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH:26]([CH3:28])[CH3:27])([CH3:22])([CH3:21])[CH3:20].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:19]([O:23][C:24](=[O:46])[C@@H:25]([NH:29][S:30]([C:33]1[CH:34]=[CH:35][C:36]([C:39]2[CH:40]=[CH:41][C:42]([NH:45][C:10]([C:8]3[O:9][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[C:14]([O:15][CH:16]([CH3:18])[CH3:17])[C:6]=4[C:7]=3[CH3:13])=[O:12])=[CH:43][CH:44]=2)=[CH:37][CH:38]=1)(=[O:32])=[O:31])[CH:26]([CH3:28])[CH3:27])([CH3:21])([CH3:22])[CH3:20]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10525284(S)-2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid tert-butyl esterHCID 687112095-Chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid

Product 1

HCID 68715589(S)-2-{4'-[(5-chloro-4-isopropoxy-3-methyl-benzofuran-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 80 mg of 5-chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid was added 121 mg of (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid tert-butyl ester, 159 mg of BOP, 46 mg of N,N-diisopropylethylamine and 4 mL of DMF. The mixture was stirred at room temperature for 48 h. The mixture was addedbrine and was extracted with ethyl acetate. The combined ethyl acetate solution was washed with brine. Removal of the solvent and purification of the residue by column chromatography on silica gel gave 178 mg (98% yield) of (S)-2-{4′-[(5-chloro-4-isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester as a colorless semi-solid.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe combined ethyl acetate solution was washed with brine
  3. customRemoval of the solvent and purification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-36cb92ce361c4066b865e619edbb120c
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

Loading…