Hydrochloric Acid → HCID 59212055, compound

HRID 655178Notes

Reaction equation

HRID 655178 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:19][C:20]([O:22]C)=[O:21])[C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C1COCC1.CO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:19][C:20]([OH:22])=[O:21])[C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59212030{(4-Bromophenyl)-[(E)-(3-phenylacryloyl)]amino}acetic acid, methyl ester

Product 1

HCID 59212055HCID 59212055, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of {(4-bromophenyl)-[(E)-(3-phenylacryloyl)]amino}acetic acid, methyl ester 1 (14.61 g, 0.39 mol) in THF (150 mL) and methanol (50 mL) was treated with lithium hydroxide (2.80 g, 0.117 mol) in water (50 mL). The reaction mixture was stirred at room temperature for 45 min and then acidified with conc. hydrochloric acid and concentrated in vacuo. The residue was diluted with ethyl acetate and washed with 10% hydrochloric acid, brine, dried (Na2SO4) and the organic solution evaporated to give the title compound as a viscous oil (13.82 g, 97%). 1HNMR (300 MHz) (CDCl3) δ 4.53 (2H, s), 6.36 (1H, d, J=16 Hz), 7.27 (2H, d), 7.3-7.4 (5H, m), 7.60 (2H, d) and 7.76 (1H, d, J=16 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 10% hydrochloric acid, brine
  4. dry with materialdried (Na2SO4)
  5. customthe organic solution evaporated

Sources & evidence

ORD record
ord-553ff634ee0343cf926a4a974c040753
Source dataset
uspto-grants-2011_12
Patent number
US08071582B2

Reaction notes

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