Hydrochloric Acid → 4-([(6-Bromo-1,3-benzothiazol-2-yl)amino]carbonylamino)butanoic acid

HRID 9163

Reaction equation

[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[O:11])[S:8][C:4]=2[CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:11])[S:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of ethyl 4-([(6-bromo-1,3-benzothiazol-2-yl)amino]carbonylamino)-butanoate (175 mg, 0.453 mmol) in THF/EtOH (1/1, 3 mL) was added 2 M NaOH (2.26 mL, 4.53 mmol). The reaction mixture was stirred at about 20° C. for about 3 hrs then 2 M HCl was added until pH<6 and a white precipitate was formed. The precipitate was filtered off and washed with H2O. 25 mg (15%) pure product was isolated.

Workup

customa white precipitate was formed
filtrationThe precipitate was filtered off
washwashed with H2O

Sources & evidence

ORD record: ord-eeb2af849bb244f29f28bc6c0698016c
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Linked notes

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