Triethylamine → 2-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(5-methyl-hexanoyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436513노트

반응식

HRID 1436513 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:38][CH:39]([CH3:46])[CH2:40][CH2:41][CH2:42][C:43](O)=[O:44].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:43](=[O:44])[CH2:42][CH2:41][CH2:40][CH:39]([CH3:46])[CH3:38])[CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 6

HCID 8471TriethylamineHCID 123445-Methylhexanoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 866153742-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 866153782-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(5-methyl-hexanoyl)-piperazine-1-carboxylic acid tert-butyl ester수율 76.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Dissolve (2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester (110 mg, 0.22 mmol) in 2.2 ml of dichloromethane and react with 5-methylhexanoic acid (28.6 mg, 0.22 mmol), EDCI (50.6 mg, 0.26 mmol), HOBT (35.6 mg, 0.26 mmol), triethylamine (0.09 ml, 0.66 mmol) and dimethylaminopyridine (2.6 mg, 0.02 mmol). Stir at room temperature overnight. Dilute with CH2Cl2, and wash with 5%NaHCO3 and saturated aqueous sodium chloride. Dry organic layers with MgSO4 and remove the solvent under reduced pressure. Subject residue to silica gel chromatography, eluting with hexanes/ethyl acetate/triethylamine 67:32:1 to obtain 103 mg (76% yield) of the desired product.

후처리

  1. washwash with 5%NaHCO3 and saturated aqueous sodium chloride
  2. customDry organic layers with MgSO4 and remove the solvent under reduced pressure
  3. washSubject residue to silica gel chromatography, eluting with hexanes/ethyl acetate/triethylamine 67:32:1

출처 및 근거

ORD 기록
ord-d8e81a93d3c84310bf95b354b81a23c9
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618978B2

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