Trifluoroacetic acid → (2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-tritylthiopyrrolidine

HRID 1034482ノート

反応式

HRID 1034482 の反応式
[N+:1]([C:4]1[CH:51]=[CH:50][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:37][NH:38][S:39]([NH:42]C(OC(C)(C)C)=O)(=[O:41])=[O:40])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[N+:1]([C:4]1[CH:51]=[CH:50][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:14][C@H:13]2[CH2:37][NH:38][S:39](=[O:40])(=[O:41])[NH2:42])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57171993(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-t-butoxycarbonylaminosulfonylaminomethyl-4-tritylthiopyrrolidine

生成物 1

HCID 57161027(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-tritylthiopyrrolidine収率 110.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-t-butoxycarbonylaminosulfonylaminomethyl-4-tritylthiopyrrolidine (1.46 g: 2 mmole) in dichloromethane (5 ml) under ice cooling, anisole (2.4 ml) and trifluoroacetic acid (3.9 ml) are added. The mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with ethyl acetate and ice water and extracted with ethyl acetate. The extract is successively washed with water and saturated brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is recrystallized from n-hexane to give (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-tritylthiopyrrolidine (1.4 g). Yield: Nearly quantitative. NMR δ(CDCl3) ppm: 1.43 to 1.70(m, 1H), 2.08 to 2.30(m, 1H), 2.65 to 3.50(m, 5H), 3.74 to 4.00(m, 1H), 5.03, 5.13(ABq, J=15 Hz, 2H), 5.73(br s, 1H), 7.00 to 7.60(m, 17H), 8.25(d, J=9 Hz, 2H). IR ν (CHCl3) cm-1 : 3334br, 1688, 1607.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract is successively washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is recrystallized from n-hexane

出典と根拠

ORDレコード
ord-99ca6137af5845e098d24095b278aead
出典データセット
uspto-grants-1994_05
特許番号
US05317016

反応ノート

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