Lithium Hydroxide → 2-[(4-Phenoxyphenyl)formamido]acetic acid

HRID 1178024Notes

Reaction equation

HRID 1178024 reaction equation
[Li+].[OH-:2].C([O:5][C:6](=[O:23])[CH2:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)C>C1COCC1.CO.O>[O:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][CH2:7][C:6]([OH:5])=[O:23])=[O:2])=[CH:11][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66953480(4-Phenoxy-benzylamino)-acetic acid ethyl ester

Product 1

HCID 24048312-[(4-Phenoxyphenyl)formamido]acetic acidYield 91.41%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (4.81 g, 114.63 mmol) was added to a stirred solution of (4-phenoxy-benzylamino)-acetic acid ethyl ester (5.72 g, 19.12 mmol) in THF:MeOH:H2O (3:1:1, 75 mL), and the resulting mixture was stirred at room temperature for 5 hrs. The MeOH and THF were evaporated, and the residue was acidified with cold 20% aqueous HCl. The resulting precipitate was filtered, washed with water and dried to afford 4.74 g (91.41% yield) of (4-phenoxy-benzoylamino)-acetic acid. 1H NMR (DMSO): δ 7.8 (d, 2H,), 7.75 (t, 1H), 7.4 (t, 2H), 7.15 (t, 1H), 7.05 (d, 2H), 7.0 (d, 2H).

Workup

  1. customThe MeOH and THF were evaporated
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-54ad4cf06c744df391fb4da63b7742ef
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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