Water → 4-[((4-Carboxybutyl){2-[(2-chlorobenzyl)oxy]phenethyl}amino)methyl]-benzoic acid

HRID 8132Notes

Reaction equation

[Cl:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][O:5][C:6]1[CH:33]=[CH:32][CH:31]=[CH:30][C:7]=1[CH2:8][CH2:9][N:10]([CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16].O.[OH-].[Na+]>CO>[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:28][CH:29]=1)[CH2:9][CH2:8][C:7]1[CH:30]=[CH:31][CH:32]=[CH:33][C:6]=1[O:5][CH2:4][C:3]1[CH:34]=[CH:35][CH:36]=[CH:37][C:2]=1[Cl:1])([OH:17])=[O:16]

Participants

Conditions

Temperature: 60 °C

Procedure

124.8 mg (0.238 mmol) of methyl 4-{[{2-[(2-chlorobenzyl)-oxy]phenethyl}(5-methoxy-5-oxopentyl)amino]methyl}benzoate from Ex. 1 are initially charged in 0.3 ml of methanol and 0.17 ml of water and admixed with 0.2 ml of a 40% strength sodium hydroxide solution. The mixture is stirred at 60° C. for one hour and then cooled, and the methanol is distilled off under reduced pressure. The aqueous phase is adjusted to pH 4 by addition of a citric acid/aqueous sodium hydroxide solution buffer and the resulting precipitate is separated off. Tituration with boiling cyclohexane gives a finely crystalline product.

Workup

temperaturecooled
distillationthe methanol is distilled off under reduced pressure
additionThe aqueous phase is adjusted to pH 4 by addition of a citric acid/aqueous sodium hydroxide solution buffer
customthe resulting precipitate is separated off
customTituration with boiling cyclohexane gives a finely crystalline product

Sources & evidence

ORD record: ord-04c146a1b0024307add260bad868c423
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087644B1

Reaction notes

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