Benzyl chloroformate → (S)-2-[Benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester

HRID 2095486Notes

Reaction equation

HRID 2095486 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][O:13][C:14](=[O:24])[C@@H:15]([NH:17][CH2:18][CH:19]([O:22][CH3:23])[O:20][CH3:21])[CH3:16].C(=O)([O-])O.[Na+]>CC(C)=O.O>[CH3:12][O:13][C:14](=[O:24])[C@@H:15]([N:17]([C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])[CH2:18][CH:19]([O:22][CH3:23])[O:20][CH3:21])[CH3:16]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 63697235(S)-2-(2,2-dimethoxy-ethylamino)-propionic acid methyl ester

Product 1

HCID 67074039(S)-2-[Benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl esterYield 72.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Benzyl chloroformate (4.46 g, 24.8 mmol) was added at 0° C. to a mixture of (S)-2-(2,2-dimethoxy-ethylamino)-propionic acid methyl ester (4.75 g, 24.8 mmol) and sodium hydrogencarbonate (4.17 g, 49.7 mmol) in acetone (25 mL) and water (25 mL). The ice bath was removed, then after 2 h the reaction mixture was poured onto ice water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient afforded the titled compound (5.84 g, 72%). Yellow oil, MS (ISP)=348.2 (M+Na)+.

Workup

  1. customThe ice bath was removed
  2. additionafter 2 h the reaction mixture was poured onto ice water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8934d0e132554b2ebca743314cb0feb5
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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