Diisopropylethylamine → (S)-2-{4'-[(4-furan-3-yl-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

HRID 29372Notes

Reaction equation

HRID 29372 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:11]3[C:12]([CH3:18])=[C:13]([C:15]([OH:17])=O)[O:14][C:10]=3[CH:9]=[CH:8][CH:7]=2)=[CH:2]1.[CH3:19][O:20][C:21](=[O:43])[C@@H:22]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=2)=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:23]([CH3:25])[CH3:24].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>[Cl-].[Na+].O.CN(C=O)C>[CH3:19][O:20][C:21](=[O:43])[C@@H:22]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[CH:38][C:39]([NH:42][C:15]([C:13]3[O:14][C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([C:3]5[CH:4]=[CH:5][O:1][CH:2]=5)[C:11]=4[C:12]=3[CH3:18])=[O:17])=[CH:40][CH:41]=2)=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:23]([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59847687(S)-2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl esterHCID 687127394-Furan-3-yl-3-methyl-benzofuran-2-carboxylic acid

Product 1

HCID 68712301(S)-2-{4'-[(4-furan-3-yl-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl esterYield 93.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 4-furan-3-yl-3-methyl-benzofuran-2-carboxylic acid (114 mg, 0.47 mmol) was added (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester (170 mg, 0.47 mmol), BOP (249 mg, 1.2 eq), N,N-diisopropylethylamine (0.1 mL, 1.2 eq) and 4 mL of DMF. The mixture was stirred at room temperature overnight. The reaction mixture was poured into brine, and extracted with ethyl acetate. The combined organic solution was washed with brine and water. Removal of the solvent gave the crude product, which was purified by column chromatography on silica gel to give 258 mg of (S)-2-{4′-[(4-furan-3-yl-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester, obtained as white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic solution was washed with brine and water
  3. customRemoval of the solvent
  4. customgave the crude product, which
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bfe91bfed36d4061bbff60efd38f0499
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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