Water → tert-Butyl 3-aminopropanoate

HRID 843721Notes

Reaction equation

HRID 843721 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][C@@H:8](CO)[NH:9]C(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.O>ClCCl>[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][NH2:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15043090(S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate

Product 1

HCID 4192171tert-Butyl 3-aminopropanoateYield 213.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of N(benzyloxycarbonyl)-3(S)-hydroxymethyl-β-alanine tert-butyl ester (3.1 g) and triethylamine (1.35 ml) in dichloromethane (25 ml) was added a solution of methanesulfonyl chloride (1.35 ml) in dichloromethane (5 ml), under ice cooling. After stirring at room temperature for 1 hour. The mixture was poured into water and extracted with dichloromethane. The extract was washed with water, brine and dried over MgSO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with CHCl3 to give N-(benzyloxycarbonyl)-3(S)-methanesulfonyloxymethyl)-β-alanine tert-butyl ester (3.1 g) as an colorless oil.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with CHCl3

Sources & evidence

ORD record
ord-d9277e655bd1474aada2e06559d3ba7e
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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