Methanol → Acetic acid, butoxy[[(phenylmethoxy)carbonyl]amino]-

HRID 1973479Notes

Reaction equation

HRID 1973479 reaction equation
C([O:5][C:6](=[O:24])[CH:7]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])CCC.CO.[Na].C(=O)([O-])[O-]>O.C(OCC)(=O)C>[CH2:12]([O:11][C:9]([NH:8][CH:7]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:6]([OH:24])=[O:5])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 19660Carbonate IonHCID 5360545SodiumHCID 10497164Acetic acid, butoxy[[(phenylmethoxy)carbonyl]amino]-, butyl ester

Product 1

HCID 10755254Acetic acid, butoxy[[(phenylmethoxy)carbonyl]amino]-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.002 mol. of N-benzyloxycarbonyl-2-n-butoxyglycine n-butyl ester is stirred with 10 ml. of methanol and 10 ml. of 5% aqueous sodium bicarbonatesodium carbonate solution for 5 hours at 25°. The reaction mixture is then diluted with water and shaken with ethyl acetate. The layers are separated and the aqueous layer is acidified to pH 2.0 and extracted with ethyl acetate containing 10% ethanol. The extracts are dried (Na2SO4) and concentrated in vacuo to give the title compound.

Workup

  1. customThe layers are separated
  2. extractionextracted with ethyl acetate containing 10% ethanol
  3. dry with materialThe extracts are dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-020004948548470e979e03c54070fed1
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

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