Sodium Carbonate → N-Boc-4-Hydroxyphenyl-DL-glycine

HRID 1973488Notes

Reaction equation

HRID 1973488 reaction equation
C([O:5][C:6](=[O:23])[CH:7]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])CCC.C(=O)([O-])[O-].[Na+].[Na+]>CO>[C:12]([O:11][C:9]([NH:8][CH:7]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:6]([OH:23])=[O:5])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 20312394N-t-butoxycarbonyl-2-(4-hydroxyphenyl)glycine n-butyl ester

Product 1

HCID 4189925N-Boc-4-Hydroxyphenyl-DL-glycine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.5 g. (1.5 mmol.) of N-t-butoxycarbonyl-2-(4-hydroxyphenyl)glycine n-butyl ester in 20 ml. of methanol and 30 ml. of 5% aqueous sodium carbonate was heated at reflux for 30 minutes. The solvent was removed in vacuo and the aqueous residue was extracted with ethyl acetate. The aqueous phase was acidified to pH 3.0 with phosphoric acid and again extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated to give N-t-butyoxycarbonyl-2-(4-hydroxyphenyl)glycine, m.p. 112°-114° (methanol-water).

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe solvent was removed in vacuo
  3. extractionthe aqueous residue was extracted with ethyl acetate
  4. extractionagain extracted with ethyl acetate
  5. dry with materialThe extract was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5504d89a74294d6c904b694bb1bbb61b
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

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