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

HRID 29442
Notes
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Reaction equation

HRID 29442 reaction equation
[Na+].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O-:13])=O)=[N:8][C:7]=2[CH:14]=1.[C:15]([O:19][C:20](=[O:42])[C@@H:21]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:22]([CH3:24])[CH3:23])([CH3:18])([CH3:17])[CH3:16].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:15]([O:19][C:20](=[O:42])[C@@H:21]([NH:25][S:26]([C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:36]=[CH:37][C:38]([NH:41][C:11]([C:9]3[O:10][C:6]4[CH:5]=[CH:4][C:3]([CH3:2])=[CH:14][C:7]=4[N:8]=3)=[O:13])=[CH:39][CH:40]=2)=[CH:33][CH:34]=1)(=[O:28])=[O:27])[CH:22]([CH3:24])[CH3:23])([CH3:17])([CH3:18])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 687130965-Methyl-benzooxazole-2-carboxylic acid sodium salt

Product 1

HCID 68711043
(S)-3-methyl-2-{4'-[(5-methyl-benzooxazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid tert-butyl ester
Yield 12.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 5-methyl-benzooxazole-2-carboxylic acid sodium salt (130 mg, 0.83 mmol) was added (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid tert-butyl ester (400 mg, 1.2 eq), BOP (430 mg, 1.2 eq), N,N-diisopropylethylamine (126 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 solution was washed with brine and water. Removal of solvent gave the crude product, which was purified by column chromatography on silica gel to give 60 mg of (S)-3-methyl-2-{4′-[(5-methyl-benzooxazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid tert-butyl ester was obtained as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic solution was 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-55eb72e3f98748e8b0c0be42e5f01ed2
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07420001B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes