Lithium Hydroxide → {[4-(Benzyloxy)phenyl]formamido}acetic acid

HRID 1178063Notes

Reaction equation

HRID 1178063 reaction equation
[Li+].[OH-].C([O:5][C:6](=[O:25])[CH2:7][NH:8][C:9](=[O:24])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)C>C1COCC1.CO.O>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][CH2:7][C:6]([OH:25])=[O:5])=[O:24])=[CH:11][CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57855660HCID 57855660, compound

Product 1

HCID 23931762{[4-(Benzyloxy)phenyl]formamido}acetic acidYield 91.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (1.32 g, 31.5 mmol) was added to a stirred solution of (4-benzyloxy-benzoylamino)-acetic acid ethyl ester (2.47 g, 7.8 mmol) in THF:MeOH:H2O (2:2:1, 50 mL). The resulting mixture was stirred at room temperature overnight. The MeOH and THF were evaporated and the residue was diluted with water (20 mL) and acidified with 10% HCl solution. The resulting precipitate was washed with water followed by hexane and dried to afford 2.03 g (90.6 yield) of (4-benzyloxy-benzoylamino)-acetic acid. 1H NMR: (DMSO) δ 7.9 (d, 2H), 7.8 (s, 1H), 7.5 (m, 5H), 7.1 (d, 2H), 5.2 (s, 2H), 3.6 (d, 2H).

Workup

  1. customThe MeOH and THF were evaporated
  2. additionthe residue was diluted with water (20 mL)
  3. washThe resulting precipitate was washed with water
  4. customdried

Sources & evidence

ORD record
ord-80e578baf5534572a20a188831385e82
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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