4-Phenylbutyric Acid → Rac-n-({[(4-chloro-phenyl)-phenyl-methyl]-carbamoyl}-methyl)-4-phenyl-butyramide

HRID 2425183Notes

Reaction equation

HRID 2425183 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH:6][CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[C:21]1([CH2:27][CH2:28][CH2:29][C:30](O)=[O:31])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH:7]([NH:6][C:4]([CH2:3][NH:2][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:5])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 47754-Phenylbutyric AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 672464382-Amino-N-[(4-chloro-phenyl)-phenyl-methyl]-acetamide hydrochloride

Product 1

HCID 59689148Rac-n-({[(4-chloro-phenyl)-phenyl-methyl]-carbamoyl}-methyl)-4-phenyl-butyramideYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.32 mmol rac-2-amino-N-[(4-chloro-phenyl)-phenyl-methyl]-acetamide hydrochloride (Example 3.1) in 5 ml acetonitrile was treated successively with 0.32 mmol 4-phenylbutyric acid, 1.61 mmol DIPEA and 0.35 mmol TBTU. The reaction mixture was stirred for 1 hour at room temperature and concentrated. Chromatography (SiO2; dichloromethane/methanol) gave the title compound as a colorless solid. Yield=71%. MS (m/e): 419.3 (MH−, 100%).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-aae752b60ace44de9d3ee19d8caf7d9e
Source dataset
uspto-grants-2011_06
Patent number
US07964645B2

Reaction notes

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