tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoate → 4-[N-(5-Bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoic acid

HRID 355778Notes

Reaction equation

HRID 355778 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(C)(C)C)=[O:25])=[CH:22][CH:21]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1>C(O)=O>[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]([C:20]1[CH:32]=[CH:31][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1

Participants

3

Reactant 1

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

Product 1

HCID 226755684-[N-(5-Bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoate (1.79 g) was suspended in formic acid (10 ml) and heated on a steam bath until a clear solution formed. The reaction mixture was cooled and stood at ambient temperature for 18 hours. The resulting solid was filtered and washed with formic acid (2×5 ml) and dried under vacuum at 60° C. to give the title product (1.4 g).

Workup

  1. temperatureheated on a steam bath until a clear solution
  2. customformed
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe resulting solid was filtered
  5. washwashed with formic acid (2×5 ml)
  6. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-84e4a0c204104a5e8487199bbce9d2dd
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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