Hydrochloric Acid → (2R,4S)-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methyl-4-mercaptopyrrolidine

HRID 1941605Notes

Reaction equation

HRID 1941605 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:7]([CH2:17][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[S:19](=[O:22])(=[O:21])[NH2:20])[CH2:6]1)(=O)C.C[O-].[Na+].C1(C)C=CC=CC=1.Cl>ClCCl.CO.O>[C:13]([O:12][C:10]([N:8]1[CH2:9][C@@H:5]([SH:4])[CH2:6][C@@H:7]1[CH2:17][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[S:19](=[O:22])(=[O:21])[NH2:20])=[O:11])([CH3:15])([CH3:16])[CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 10942334Sodium MethoxideHCID 57156698(2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine2×

Product 1

HCID 10549579(2R,4S)-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methyl-4-mercaptopyrrolidine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine (i.e., a substrate) in dichloromethane, 4.92M sodium methoxide (NaOMe) in methanol is added. The mixture is stirred. The conditions for this reaction are shown in Table 3, Step A-7. The reaction mixture is diluted with water. The water layer is taken, toluene is added thereto, and acidified with conc. hydrochloric acid under ice cooling. The organic layer is taken, successively washed with water and saturated brine, dried over magnesium sulfate, and concentrated in vacuo to give (2R,4S)-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methyl-4-mercaptopyrrolidine. mp. 90.0° to 91.5° C.

Workup

  1. washsuccessively washed with water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b70a702b7eb746cc8feb8de3ba3b0592
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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