Sodium Hydroxide → HCID 5818841, compound

HRID 1864029Notes

Reaction equation

HRID 1864029 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:19])[CH2:6][NH:7][C:8](=[O:18])/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17]>O.C(O)C>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1/[CH:10]=[CH:9]/[C:8]([NH:7][CH2:6][C:5]([OH:19])=[O:4])=[O:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 37911841HCID 37911841, compound

Product 1

HCID 5818841HCID 5818841, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (400 mg, 10.0 mmol) of sodium hydroxide in water (2 ml) was added to a solution of (2.34 g, 9.9 mmol) of (E)-2-(3-(2-fluorophenyl)acrylamido)acetic acid methyl ester in ethanol (50 ml). The reaction solution was stirred for 1 h at RT and then concentrated in vacuo. The residue was taken up in water and washed twice with ethyl acetate. The aqueous phase was then adjusted carefully to pH 4 with 3% hydrochloric acid, and extraction with ethyl acetate was carried out. The organic phase was concentrated in vacuo, 1.22 g (5.5 mmol, 55%) of (E)-2-(3-(2-fluorophenyl)acryl-amido)acetic acid (S7) being obtained as residue.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed twice with ethyl acetate
  3. extractionThe aqueous phase was then adjusted carefully to pH 4 with 3% hydrochloric acid, and extraction with ethyl acetate
  4. custombeing obtained as residue

Sources & evidence

ORD record
ord-d56f45b961b0471b8f4ee5905c4d5564
Source dataset
uspto-grants-2009_12
Patent number
US07625900B2

Reaction notes

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