Ethyl Acetate → Benzyl 1-mercapto-2-methylpropan-2-ylcarbamate

HRID 2061055Notes

Reaction equation

HRID 2061055 reaction equation
C(=O)([S:3][CH2:4][C:5]([NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])([CH3:7])[CH3:6])C.[OH-].[Na+].C(OCC)(=O)C>CO>[SH:3][CH2:4][C:5]([NH:8][C:9](=[O:10])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 24787377S-2-(Benzyloxycarbonylamino)-2-methylpropyl ethanethioate

Product 1

HCID 59614731Benzyl 1-mercapto-2-methylpropan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of S-2-(Benzyloxycarbonylamino)-2-methylpropyl ethanethioate (4.75 g, 16.9 mmol) in methanol (35 mL) was mixed with a 5 N sodium hydroxide solution (3 equiv, 50 mL, 50.7 mmol) and stirred at RT for 15 min. TLC (20% ethyl acetate in hexanes) analysis of reaction mixture indicated all the starting material was consumed. The organic solvent was removed under reduced pressure and the resulting aqueous solution was made acidic (˜pH 3) with 6 N HCl (9 mL) while cooled in an ice bath. The aqueous suspension was extracted with ethyl acetate (3×100 mL) and the combined organic layer dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give benzyl 1-mercapto-2-methylpropan-2-ylcarbamate as a pale yellow oil, 4.6 g. This material was used without any further purification.

Workup

  1. customwas consumed
  2. customThe organic solvent was removed under reduced pressure
  3. temperaturewhile cooled in an ice bath
  4. extractionThe aqueous suspension was extracted with ethyl acetate (3×100 mL)
  5. dry with materialthe combined organic layer dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b91cce98774c44f3b71ce7ffb8309174
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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