Dicyclohexylcarbodiimide → (S)-1-((S)-2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-3-hydroxybutan-1-one

HRID 1423141

반응식

HRID 1423141 반응식
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:28][C@@H:29]([CH3:34])[CH2:30][C:31](O)=[O:32].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:31](=[O:32])[CH2:30][C@@H:29]([OH:28])[CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 94318(S)-3-hydroxybutyric acidHCID 16725642HCID 16725642, 화합물

생성물 1

HCID 52918529(S)-1-((S)-2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-3-hydroxybutan-1-one수율 57%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (92 mg, 0.25 mmol) in CH2Cl2 (1 mL) at 0-5° C. was treated with (S)-3-hydroxybutanoic acid (29 mg, 0.28 mmol), a catalytic amount of DMAP, and DCC (57 mg, 0.28 mmol). The reaction mixture was allowed to warm to room temperature and stir 6 h. After this time the reaction mixture was evaporated and the residue purified by silica gel flash chromatography with 50% EtOAc/hexanes as eluant to afford the title compound as an oil (64 mg, 57%). LC/MS (Method B) 3.53 min, [M+1]+ 453.

후처리

  1. customAfter this time the reaction mixture was evaporated
  2. customthe residue purified by silica gel flash chromatography with 50% EtOAc/hexanes as eluant

출처 및 근거

ORD 기록
ord-b678120f363c45b8a50feff5dafe9914
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927546B2

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