Sodium Hydroxide → Tert-butyl [2-(benzylthio)-3,3-dimethoxypropyl]carbamate

HRID 2239025Notes

Reaction equation

HRID 2239025 reaction equation
[CH2:1]([S:8][CH:9]([CH:12]([O:15][CH3:16])[O:13][CH3:14])[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:19](=O)([OH:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[CH2:1]([S:8][CH:9]([CH:12]([O:13][CH3:14])[O:15][CH3:16])[CH2:10][NH:11][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3015642Mono-tert-butyl carbonateHCID 574759902-(Benzylthio)-3,3-dimethoxypropan-1-amine

Product 1

HCID 59136115Tert-butyl [2-(benzylthio)-3,3-dimethoxypropyl]carbamateYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(Benzylthio)-3,3-dimethoxypropan-1-amine (1 g) was dissolved in tetrahydrofuran (7 mL), and 1N aqueous sodium hydroxide solution (10 mL) was added. A solution of t-butyl bicarbonate (993 mg) in tetrahydrofuran (3 mL) was added dropwise to the reaction solution under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, and dried over sodium sulfate. The obtained solution was filtrated through basic silica gel, and concentrated to give the title compound (1.39 g, yield 99%) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe obtained solution was filtrated through basic silica gel
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d278bd9a1314e6b8b6fbb98a6ea68e0
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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