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

HRID 1770680Notes

Reaction equation

HRID 1770680 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 (10.60 g, 35.88 mmol, prepared as described in WO 2008/083347) in methanol (100 ml) was added 5.0 M NaOH in H2O (15 ml, 75 mmol). The solution was stirred for 2 hour, concentrated in vacuo, and the residue suspended in ethyl acetate (300 ml), washed with 3×100 ml 5% NaHSO4, 1×100 ml saturated NaCl, dried on MgSO4, and concentrated in vacuo. The material was used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with 3×100 ml 5% NaHSO4, 1×100 ml saturated NaCl
  3. customdried on MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe material was used without further purification

Sources & evidence

ORD record
ord-44907ea7d63942c3bf030d54e364d58d
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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