Hydrochloric Acid → {(4-Hydroxyphenyl)-[(E)-(3-phenylacryloyl)]amino}acetic acid

HRID 2243990노트

반응식

HRID 2243990 반응식
[OH-].[Li+].C[O:4][C:5]([CH2:7][N:8]([C:26](=[O:35])/[CH:27]=[CH:28]/[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:9]1[CH:14]=[CH:13][C:12]([O:15]C(=O)/C=C/C2C=CC=CC=2)=[CH:11][CH:10]=1)=[O:6].Cl>O.C1COCC1.CO>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]([CH2:7][C:5]([OH:6])=[O:4])[C:26](=[O:35])/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:10][CH:11]=1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2회HCID 59212038(E)-3-Phenylacrylic acid 4-{methoxycarbonylmethyl-[(E)-(3-phenylacryloyl)]-amino}phenyl ester

생성물 1

HCID 59212013{(4-Hydroxyphenyl)-[(E)-(3-phenylacryloyl)]amino}acetic acid수율 75%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hydroxide (119 mg, 4.96 mmol) in water (10 mL) was added to a solution of (E)-3-phenylacrylic acid 4-{methoxycarbonylmethyl-[(E)-(3-phenylacryloyl)]-amino}phenyl ester 12 (734 mg, 1.66 mmol) in THF (30 mL) and methanol (10 mL). The reaction mixture was stirred at room temperature for 2 h. A further quantity of lithium hydroxide (119 mg, 4.96 mmol) in water (5 mL) was added and the reaction mixture stirred for a further 1 h. It was then acidified to pH1 with conc. hydrochloric acid and concentrated in vacuo. The aqueous mixture was extracted with ethyl acetate (×2) and the organic layers combined, washed with brine, dried (Na2SO4) and evaporated. The resultant residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate, to afford the title compound (0.37 g, 75%). 1HNMR (300 MHz) (d6-DMSO) δ 4.07 (2H, br s), 6.37 (1H, d, J=15 Hz), 6.78 (2H, d), 7.22 (2H, d), 7.34 (5H, m) and 7.44 (1H, d, J=15 Hz).

후처리

  1. stirringthe reaction mixture stirred for a further 1 h
  2. concentrationconcentrated in vacuo
  3. extractionThe aqueous mixture was extracted with ethyl acetate (×2)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe resultant residue was purified by flash column chromatography on silica gel
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-323cca35179c48acac63d8eaee6ab1ae
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678785B2

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