Ethyl Acetate → (2S,4R)-4-methanesulfonyloxy-2-(thiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37251

反応式

HRID 37251 の反応式
Br[CH2:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16])=O.[CH:28]([NH2:30])=[S:29].C(OCC)(=O)C>CO.ClCCl>[CH3:14][S:11]([O:10][C@H:8]1[CH2:7][N:6]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[C@H:5]([C:3]2[N:30]=[CH:28][S:29][CH:2]=2)[CH2:9]1)(=[O:12])=[O:13]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 3005587MethanethioamideHCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

生成物 1

HCID 14305075(2S,4R)-4-methanesulfonyloxy-2-(thiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine収率 88%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of (2S, 4R)-2-bromoacetyl-4-methane-sulfonyloxy-1- (4-nitrobenzyloxycarbonyl)pyrrolidine(1.15 g) in a mixture of methanol (20 ml) and dichloromethane (15 ml) was added thioformamide (453 mg) at room temperature. After stirring at the same temperature for 4 hours, the mixture was poured into ethyl acetate and washed in turn with saturated aqueous sodium bicarbonate and brine. The dried organic layer was evaporated and the resulting oil was crystallized from a mixture of n-hexane and dichloromethane (100:1 V/V) to give (2S, 4R) -4-methanesulfonyloxy-2-(thiazol-4-yl)-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (930 mg).

後処理

  1. washwashed in turn with saturated aqueous sodium bicarbonate and brine
  2. customThe dried organic layer was evaporated
  3. customthe resulting oil was crystallized from a mixture of n-hexane and dichloromethane (100:1 V/V)

出典と根拠

ORDレコード
ord-023370ae923f417cb88f524b72199bb7
出典データセット
uspto-grants-1995_05
特許番号
US05420122

関連ノート

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