Triphenylphosphine → [(3R)-3-[(2,5-Dichlorophenyl)thio]-3-(2-thiazolyl)propyl]carbamic acid 1,1-dimethylethyl ester

HRID 966963

반응식

HRID 966963 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[SH:9].[CH3:10][C:11]([O:14][C:15](=[O:26])[NH:16][CH2:17][CH2:18][C@H:19](O)[C:20]1[S:21][CH:22]=[CH:23][N:24]=1)([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.CCCC(C)C.C(OCC)(=O)C>[CH3:13][C:11]([O:14][C:15](=[O:26])[NH:16][CH2:17][CH2:18][C@@H:19]([S:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Cl:1])[C:20]1[S:21][CH:22]=[CH:23][N:24]=1)([CH3:10])[CH3:12]

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 799652,5-DichlorobenzenethiolHCID 69799613[(3S)-3-Hydroxy-3-(2-thiazolyl)propyl]carbamic acid 1,1-dimethylethyl ester

생성물 1

HCID 86759856[(3R)-3-[(2,5-Dichlorophenyl)thio]-3-(2-thiazolyl)propyl]carbamic acid 1,1-dimethylethyl ester수율 21%

시약·촉매·용매 3

HCID 78922-Methylpentane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2,5-dichlorothiophenol (179 mg, 1 mmol), [(3S)-3-hydroxy-3-(2-thiazolyl)propyl]carbamic acid 1,1-dimethylethyl ester (258 mg, 1 mmol) and triphenylphosphine (315 mg, 1.2 mmol) in dry tetrahydrofuran (30 ml) at 0° C. under nitrogen, was added diisopropyl azodicarboxylate (243 mg, 0.24 ml, 1.2 mmol) dropwise over 5 minutes. The mixture was stirred at room temperature for 16 h, then concentrated in vacuo to leave a crude yellow gum. Flash chromatography (silica, 15% ethyl acetate in isohexane) afforded a clear oil (85 mg, 21%).

후처리

  1. concentrationconcentrated in vacuo
  2. customto leave a crude yellow gum

출처 및 근거

ORD 기록
ord-b7d71d8b2993495cb1602eda97538b96
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953797B2

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