Water → N-Boc-p-hydroxyphenylglycine

HRID 917977Notes

Reaction equation

HRID 917977 reaction equation
[CH:1]1[C:6]([C@@H](N)C(O)=O)=[CH:5][CH:4]=[C:3]([OH:12])[CH:2]=1.[C:13]([O:17][C:18]([N:20]=[N+]=[N-])=[O:19])([CH3:16])([CH3:15])[CH3:14].[OH2:23].[O:24]1[CH2:29][CH2:28]OCC1>>[C:13]([O:17][C:18]([N:20]([C:6]1[CH:1]=[CH:2][C:3]([OH:12])=[CH:4][CH:5]=1)[CH2:28][C:29]([OH:24])=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 89853D-p-hydroxyphenylglycine

Product 1

HCID 21896684N-Boc-p-hydroxyphenylglycine

Procedure

An intimate mixture of D-p-hydroxyphenylglycine (3.34 g., 0.02 mol.) and MgO (1.61 g., 0.04 mol.) was suspended in 50% aqueous dioxane with stirring and T-butoxycarbonyl azide (5.72 g., 0.04 mol.) was added along with additional solvent (10 ml.). The reaction mixture was heated with stirring at 50° for 18 hours and then poured into cold water (250 ml.). The resultant solution was filtered, decolorized and extracted with ethyl acetate. The aqueous phase was covered with fresh ethyl acetate, cooled to 5°, and adjusted to pH 2.9 with 40% H3PO4. The aqueous layer was separated and re-extracted with ethyl acetate. The organic extracts were combined, dried and evaporated to give the N-t-butoxycarbonyl-p-hydroxyphenyl-glycine.

Workup

  1. temperatureThe reaction mixture was heated
  2. stirringwith stirring at 50° for 18 hours
  3. filtrationThe resultant solution was filtered
  4. extractionextracted with ethyl acetate
  5. temperaturecooled to 5°
  6. customThe aqueous layer was separated
  7. extractionre-extracted with ethyl acetate
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-bb98637b50ad470085aa95966cfdebf5
Source dataset
uspto-grants-1976_07
Patent number
US03968226

Reaction notes

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