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

HRID 966963

反応式

HRID 966963 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 78922-Methylpentane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-b7d71d8b2993495cb1602eda97538b96
出典データセット
uspto-grants-2005_10
特許番号
US06953797B2

関連ノート

読み込み中…