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

HRID 468610ノート

反応式

HRID 468610 の反応式
[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

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2 回HCID 59212038(E)-3-Phenylacrylic acid 4-{methoxycarbonylmethyl-[(E)-(3-phenylacryloyl)]-amino}phenyl ester

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5a4f114100d24599a868dffd4b21ecdc
出典データセット
uspto-grants-2014_01
特許番号
US08624022B2

反応ノート

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