Hydrochloric Acid → HCID 22881090, compound

HRID 725941Notes

Reaction equation

HRID 725941 reaction equation
C([S:4][CH2:5][C@@H:6]1[CH2:10][C@@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:8][N:7]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=O)C.[OH-].[Na+].Cl>CO>[C:22]([O:21][C:19]([N:7]1[CH2:8][C@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:10][C@H:6]1[CH2:5][SH:4])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57058720HCID 57058720, compound

Product 1

HCID 22881090HCID 22881090, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,4R)-2-acetylthiomethyl-N-t-butoxycarbonyl-4-t-butyldimethylsiloxypyrrolidine (3.9 g, 10 mmol) in methanol (50 ml), 1N aqueous NaOH (11.0 ml, 11 mmol) was added in nitrogen stream under cooling with ice. The resulting solution was stirred for 30 minutes, then brought together with 1N aqueous HCl (12.0 ml, 12 mmol), and concentrated in vacuo. The resulting residue was poured into a liquid mixture of ethyl acetate with water. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a crude product of (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-mercaptomethylpyrrolidine.

Workup

  1. temperatureunder cooling with ice
  2. concentrationconcentrated in vacuo
  3. additionThe resulting residue was poured into a liquid mixture of ethyl acetate with water
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d512e37b975949f6aaa826177cefa643
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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