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

HRID 1034482노트

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HRID 1034482 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-99ca6137af5845e098d24095b278aead
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05317016

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