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

HRID 1034482Notes

Reaction equation

HRID 1034482 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-99ca6137af5845e098d24095b278aead
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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