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

HRID 1770714Notes

Reaction equation

HRID 1770714 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.CO.[OH-].[Na+]>C(OCC)(=O)C>[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 887MethanolHCID 14798Sodium HydroxideHCID 86665510S-3-(benzyloxycarbonylamino)-3-methylbutyl ethanethioate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

S-3-(Benzyloxycarbonylamino)-3-methylbutyl ethanethioate (3.00 g, 10.2 mmol) was dissolved into methanol (100 mL). Sodium hydroxide solution (5 N, 6.1 mL, 30.6 mmol) was added to the solution in one portion and stirred at room temperature for 1 hour. Thin-layer chromatography (40% ethyl acetate in hexanes) analysis of reaction mixture indicated all the starting material was consumed. The organic solvent was removed and the resulting aqueous solution was made acidic (˜pH 5) with 1 N HCl, while cooled in an ice bath. The aqueous suspension was extracted with ethyl acetate (2×100 mL) and the combined organic layer washed with water (50 mL) and brine (50 mL), dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil (2.83 g, quant). The material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.29 (s, 6H), 2.02 (m, 2H), 2.48-2.5 (m, 2H), 2.83 (t, 20 Hz, 2H), 3.60 (t, 20 Hz, 2H), 4.63 (br s, 2H), 5.05 (s, 2H), 7.29-7.37 (m, 5H). LRMS (ESI/APCI) m/z 316 [M+H]+.

Workup

  1. customwas consumed
  2. customThe organic solvent was removed
  3. temperaturewhile cooled in an ice bath
  4. extractionThe aqueous suspension was extracted with ethyl acetate (2×100 mL)
  5. washthe combined organic layer washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a pale yellow oil (2.83 g, quant)
  9. customThe material was used without further purification

Sources & evidence

ORD record
ord-6bb310414b044225bdd868b0221835ad
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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