Sodium Hydroxide → tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-carboxybenzyl)-amino]benzoate

HRID 1106791Notes

Reaction equation

HRID 1106791 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:6]([CH:33]=1)[CH2:7][N:8]([C:20]1[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][CH:21]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][CH:11]=1.[OH-].[Na+]>CO.O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[C:6]([CH:33]=1)[CH2:7][N:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][CH:15]=1)[C:20]1[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22675539tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoate

Product 1

HCID 22675508tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-carboxybenzyl)-amino]benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoate (from example 16) was dissolved in a solution of methanol (10 ml) and tetrahydrofuran (10 ml). To this solution was added aqueous 2N sodium hydroxide (3 ml) and the solution stirred at ambient temperature for 18 hours. The volume of the reaction mixture was reduced by evaporation to half the original volume, water (20 ml) was added and the mixture acidified with acetic acid. The resulting solid was filtered and dried under vacuum at 60° C. to give the title compound (12 g) m.p. 110° C.

Workup

  1. customThe volume of the reaction mixture was reduced by evaporation to half the original volume, water (20 ml)
  2. additionwas added
  3. filtrationThe resulting solid was filtered
  4. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-559ce1e4282e4923ad498ad8ed9ae192
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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