Sodium Hydroxide → HCID 10644171, compound

HRID 322849Notes

Reaction equation

HRID 322849 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[CH:19][C:10]=1[C:11]([NH:13][CH2:14][C:15]([O:17]C)=[O:16])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:20]=[CH:19][C:10]=1[C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10787454HCID 10787454, compound

Product 1

HCID 10644171HCID 10644171, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methyl N-(2,4-dibenzyloxybenzoyl)glycinate (900 mg) in methanol (20 mL) is treated with 1 M NaOH (20 mL) and stirred at 25° C. for 2 hours. The solution is evaporated, the residue diluted with water, brought to pH 1 and extracted with ethyl acetate. The extract is dried and evaporated. The residue is recrystallized from methanol to yield N-(2,4-dibenzyloxybenzoyl)glycine as a colourless solid (300 mg), m.p. 183° C. H NMR (CDCl3) 4.15(2H,d), 5.05 (2H,s), 5.2(2H,s), 6.6(1H,s), 6.7(1H,d), 7.3-7.5(10H,m), 8.2(1H,d), 8.4(1H,t).

Workup

  1. customThe solution is evaporated
  2. additionthe residue diluted with water
  3. extractionextracted with ethyl acetate
  4. customThe extract is dried
  5. customevaporated
  6. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-27d4c5d9c7774501a70696183c432364
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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