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

HRID 29434Notes

Reaction equation

HRID 29434 reaction equation
[Na+].[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]([O-:13])=O.[C:14]([O:18][C:19](=[O:41])[C@@H:20]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH:21]([CH3:23])[CH3:22])([CH3:17])([CH3:16])[CH3:15].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>[C:14]([O:18][C:19](=[O:41])[C@@H:20]([NH:24][S:25]([C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:35]=[CH:36][C:37]([NH:40][C:11]([C:3]3[O:2][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[N:4]=3)=[O:13])=[CH:38][CH:39]=2)=[CH:32][CH:33]=1)(=[O:27])=[O:26])[CH:21]([CH3:23])[CH3:22])([CH3:16])([CH3:17])[CH3:15]

Participants

7

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 53229935HCID 53229935, compound

Product 1

HCID 68714449(S)-3-methyl-2-{4'-[(benzoxazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid tert-butyl esterYield 22.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To benzooxazole-2-carboxylic acid sodium salt (161 mg, 1 mmol) was added (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid tert-butyl ester (405 mg, 1 eq), BOP (550 mg, 1.2 eq), N,N-diisopropylethylamine (155 mg, 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 layers were washed with brine and water. Removal of solvent gave the crude product, which was purified by column chromatography on silica gel to give 126 mg of (S)-3-methyl-2-{4′-[(benzoxazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid tert-butyl ester as a white solid.

Workup

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

Sources & evidence

ORD record
ord-9df6b4fe404240d2a6415376f92d1d91
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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