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

HRID 468610Notes

Reaction equation

HRID 468610 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5a4f114100d24599a868dffd4b21ecdc
Source dataset
uspto-grants-2014_01
Patent number
US08624022B2

Reaction notes

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