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

HRID 1731035
Notes
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Reaction equation

HRID 1731035 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.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O>[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 10791Sodium SesquicarbonateHCID 10497164Acetic acid, butoxy[[(phenylmethoxy)carbonyl]amino]-, butyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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 bicarbonate-sodium carbonate solution for five 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-2a272fd29a8f4b8083c15ed5cb0a8322
Source dataset
uspto-grants-1976_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03994954

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes