Triethylamine → N-Boc-p-hydroxyphenylglycine

HRID 37461

반응식

HRID 37461 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:20]([O:24][C:25](SC1N=C(C)C=C(C)N=1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>O.O1CCOCC1>[C:25]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:9][C:10]([OH:12])=[O:11])([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 67149N-(4-Hydroxyphenyl)glycineHCID 148428O-(1,1-Dimethylethyl) S-(4,6-dimethyl-2-pyrimidinyl) carbonothioate

생성물 1

HCID 21896684N-Boc-p-hydroxyphenylglycine

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

To 33.4 g (0.2 mol) of p-hydroxyphenylglycine were added 110 ml of water, 42 ml (1.5 eq.) of triethylamine, 52.8 g (1.1 eq.) of S-t-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine and 110 ml of dioxane, and the mixture was stirred at room temperature for 14 hours. To the reaction mixture was added 300 ml of water, and the mixture was extracted with 400 ml of ethyl acetate. The organic layer was extracted with 100 ml of a 5% aqueous solution of sodium hydrogencarbonate. The aqueous layers were combined, adjusted to pH 3 with 5N hydrochloric acid under ice-cooling and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of potassium hydrogensulfate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The solvent was distilled off. The thus-obtained crystals were collected by filtration with ethyl acetate/hexane. Yield: 46.0 g (86.1%).

후처리

  1. extractionthe mixture was extracted with 400 ml of ethyl acetate
  2. extractionThe organic layer was extracted with 100 ml of a 5% aqueous solution of sodium hydrogencarbonate
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous solution of potassium hydrogensulfate
  6. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. filtrationThe thus-obtained crystals were collected by filtration with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-ebc2486f05974e7d85e113f967e5ed1d
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420275

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