Sodium Hydroxide → HCID 57183904, compound

HRID 1034505Notes

Reaction equation

HRID 1034505 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([S:16]C(=O)C)[CH2:13][C@H:12]2[CH2:20][NH:21][S:22](=[O:25])(=[O:24])[NH2:23])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+]>ClCCl.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([SH:16])[CH2:13][C@H:12]2[CH2:20][NH:21][S:22](=[O:24])(=[O:25])[NH2:23])=[O:10])=[CH:26][CH:27]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 57262936HCID 57262936, compound

Product 1

HCID 57183904HCID 57183904, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-acetylthio-2-sulfamoylaminomethylpyrrolidine (982 mg: 2.35 mmole) in a mixture of dichloromethane (2 ml) and methanol (10 ml), 1N-sodium hydroxide (2.8 ml) is added under ice cooling. The mixture is stirred for 15 minutes. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is successively washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene:ethyl acetate=1:2) to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-mercapto-2-sulfamoylaminomethylpyrrolidine (783 mg). Yield: 89%. NMR δ(CDCl3) ppm: 1.6 to 2.0(m, 2H), 2.4 to 2.7(m, 1H), 3.1 to 3.8(m, 4H), 3.81(s, 3H), 3.9 to 4.2(m, 2H), 4.6 to 5.0(m, 2H), 5.04(s, 2H), 5.97(br s, 1H), 6.89(d, J=8.6 Hz, 2H), 7.30(d, J=8.6 Hz, 2H). IR ν (CHCl3) cm-1 : 3668, 3424, 1683.

Workup

  1. additionis added under ice cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract is successively washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel column chromatography (toluene:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-ca267d67158f41459427859363a9d7dd
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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