Ethyl Acetate → (2S,4R)-2-[2-(N-t-butoxycarbonylamino) methylthiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1649829ノート

反応式

HRID 1649829 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.[C:28]([O:32][C:33]([NH:35][CH2:36][C:37]([NH2:39])=[S:38])=[O:34])([CH3:31])([CH3:30])[CH3:29].C(OCC)(=O)C>CO.ClCCl>[C:28]([O:32][C:33]([NH:35][CH2:36][C:37]1[S:38][CH:2]=[C:3]([C@@H:5]2[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]2[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])[N:39]=1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 5324304tert-butyl N-(carbamothioylmethyl)carbamateHCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

生成物 1

HCID 57303896(2S,4R)-2-[2-(N-t-butoxycarbonylamino) methylthiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine収率 40.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (20 g) in a mixture of methanol (200 ml) and dichloromethane (200 ml) was added 2-(N-t-butoxycarbonylamino)thioacetamide (20 g) at room temperature. After stirring at ambient temperature for 12 hours, the mixture was poured into ethyl acetate, washed with saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated, and the obtained oil was subjected to a column chromatography on silica gel and eluted with a mixture of acetone and dichloromethane (1:5, V/V) to give (2S,4R)-2-[2-(N-t-butoxycarbonylamino)methylthiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (9.7 g).

後処理

  1. washwashed with saturated sodium bicarbonate and brine successively
  2. customThe dried organic layer was evaporated
  3. washeluted with a mixture of acetone and dichloromethane (1:5, V/V)

出典と根拠

ORDレコード
ord-fc8e683591ae4dfc80bc240d51c1adba
出典データセット
uspto-grants-1990_05
特許番号
US04921852

反応ノート

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