Hydrochloric Acid → N-Benzyloxycarbonyl-3-carboxymethyloxy-4-methoxybenzylamine

HRID 583103Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CO.Cl>O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][C:23]([OH:25])=[O:24])[CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture comprising 23.56 of N-benzyloxycarbonyl-3-ethoxycarbonylmethyloxy-4-methoxybenzylamine, 7.29 g of sodium hydroxide, 300 ml of methanol and 30 ml of water, was stirred at 60° C. for one hour. The reaction solution was neutralized by an addition of hydrochloric acid, and the solvent was distilled off under reduced pressure. Dilute hydrochloric acid was added to the obtained residue, and the mixture was extracted with chloroform. The extract layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off. The obtained residue was crystallized from diethyl ether/n-hexane to obtain 21.55 g of the above-identified compound as white crystals.

Workup

distillationthe solvent was distilled off under reduced pressure
additionDilute hydrochloric acid was added to the obtained residue
extractionthe mixture was extracted with chloroform
washThe extract layer was washed with water
dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
distillationThe solvent was distilled off
customThe obtained residue was crystallized from diethyl ether/n-hexane

Sources & evidence

ORD record: ord-0110504906d449ea98663f4fd4aa90b8
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05929074

Reaction notes

Loading…