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

HRID 1960422Notes

Reaction equation

HRID 1960422 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>[C:21]([O:20][C:19](=[O:25])[NH:11][CH2:10][CH:9]([S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:12]([O:13][CH3:14])[O:15][CH3:16])([CH3:24])([CH3:23])[CH3:22]

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-f079c2e158344174a2b8b13786be1d7f
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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