Potassium Carbonate → 2-([(Benzyloxy)carbonyl]amino)-3-methoxypropanoic acid

HRID 1882738Notes

Reaction equation

HRID 1882738 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH2:5][O:6][CH3:7].C([O-])([O-])=O.[K+].[K+]>CO>[C:9]([NH:8][CH:4]([CH2:5][O:6][CH3:7])[C:3]([OH:19])=[O:2])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 12344754Methyl 2-(((benzyloxy)carbonyl)amino)-3-methoxypropanoate

Product 1

HCID 123447572-([(Benzyloxy)carbonyl]amino)-3-methoxypropanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 10 (0.58 g) was dissolved in 80% aqueous methanol (3.0 mL). To this solution was added anhydrous K2CO3 (0.5 g) and the reaction mixture was stirred at room temperature (8 hours). The methanol was evaporated in vacuo and the residue suspended in water (50 mL). The aqueous suspension was washed with ethyl ether (2×25 mL) and then acidified to pH 3.0 using 5N HCl. The acidified aqueous phase was extracted with ethyl acetate (3×25 mL). The ethyl acetate extracts were combined, dried (Na2SO4), filtered, and evaporated in vacuo to obtain pure 11 as a clear viscous oil (0.52 g, 95%): Rf0.30 (10% MeOH/CHCl3).

Workup

  1. customThe methanol was evaporated in vacuo
  2. washThe aqueous suspension was washed with ethyl ether (2×25 mL)
  3. extractionThe acidified aqueous phase was extracted with ethyl acetate (3×25 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-50b1fd701d82499f84ab01064d6b0e07
Source dataset
uspto-grants-2004_07
Patent number
USRE038551E1

Reaction notes

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