Water → N-Boc-p-hydroxyphenylglycine

HRID 917977

반응식

HRID 917977 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

HCID 21896684N-Boc-p-hydroxyphenylglycine

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bb98637b50ad470085aa95966cfdebf5
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03968226

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