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

HRID 1106818Notes

Reaction equation

HRID 1106818 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:6]([CH:32]=1)[CH2:7][N:8]([CH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17]C(C)(C)C)=[O:16])=[CH:11][CH:10]=1>C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[C:6]([CH:32]=1)[CH2:7][N:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1)[CH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1

Participants

3

Reactant 1

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

Product 1

HCID 226755324-[N-(5-Bromo-2-benzyloxybenzyl)-N-(4-carboxybenzyl)amino]benzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-carboxybenzyl)-amino]benzoate (example 3) (500 mg) was suspended in formic acid (2 ml) and heated on a steam bath until a clear solution was obtained. This solution was left at ambient temperature for 18 hours and the resulting solid filtered, washed with formic acid (2×1 ml) and dried under vacuum at 60° C. to give the title product (340 mg) m.p. 271° C.

Workup

  1. temperatureheated on a steam bath until a clear solution
  2. customwas obtained
  3. filtrationthe resulting solid filtered
  4. washwashed with formic acid (2×1 ml)
  5. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-064d5557f5ee4070a27699ac79686242
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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