Water → Benzyl 4-mercapto-2-methylbutan-2-ylcarbamate

HRID 1770688Notes

Reaction equation

HRID 1770688 reaction equation
C(=O)([S:3][CH2:4][CH2:5][C:6]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([CH3:8])[CH3:7])C.[OH-].[Na+].O>CO>[SH:3][CH2:4][CH2:5][C:6]([NH:9][C:10](=[O:11])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86665510HCID 86665510, compound

Product 1

HCID 86665509Benzyl 4-mercapto-2-methylbutan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of S-3-(benzyloxycarbonylamino)-3-methylbutyl ethanethioate (45.0 g, 152 mmol, prepared as described in WO 2008/083347) in methanol (300 ml) was added 5.0 M NaOH in H2O (60.0 ml, 300 mmol). The solution was stirred for 1 hour, concentrated in vacuo, diluted with saturated NaHSO4 (200 ml), filtered through a coarse glass funnel, and extracted with 5×100 ml ethyl acetate. The organic layers were combined, washed with 100 ml saturated NaCl, dried on MgSO4, and concentrated in vacuo. The residue was used without further purification (24.10 g, 95.1 mmol, 63%).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with saturated NaHSO4 (200 ml)
  3. filtrationfiltered through a coarse glass funnel
  4. extractionextracted with 5×100 ml ethyl acetate
  5. washwashed with 100 ml saturated NaCl
  6. customdried on MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was used without further purification (24.10 g, 95.1 mmol, 63%)

Sources & evidence

ORD record
ord-de7f62a61ade46e29d95d2c0be8c08a3
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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