Sodium Hydroxide → 4-[2-(4-Tert-butoxycarbonylpiperazin-1-yl)thiazol-4-ylmethoxy]benzoic acid

HRID 1016474Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:30]=[CH:29][C:8]([O:9][CH2:10][C:11]2[N:12]=[C:13]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[S:14][CH:15]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1.O>[C:25]([O:24][C:22]([N:19]1[CH2:18][CH2:17][N:16]([C:13]2[S:14][CH:15]=[C:11]([CH2:10][O:9][C:8]3[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:30][CH:29]=3)[N:12]=2)[CH2:21][CH2:20]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of tert-butyl 4-[4-(4-methoxycarbonylphenoxymethyl)thiazol-2-yl]piperazine-1-carboxylate (820 mg, 1.89 mmol) in methanol (30 mL) and THF (10 mL) was treated with a solution of sodium hydroxide (226 mg, 5.67 mmol) in water (10 mL). The mixture was stirred at 55° C. for 8 hours and then concentrated by evaporation. The aqueous solution was diluted with water (10 mL) and the dilution was acidified with dilute hydrochloric acid. A resulting solid was collected by filtration to provide 4-[2-(4-tert-butoxycarbonylpiperazin-1-yl)thiazol-4-ylmethoxy]benzoic acid (800 mg, 100% yield). HNMR (dmso-d6): 7.88 (2H, d), 7.09 (2H, d), 6.91 (1H, s), 4.99 (2H, s) 3.44 (8H, m), 1.41 (9H, s).

Workup

concentrationconcentrated by evaporation
additionThe aqueous solution was diluted with water (10 mL)
filtrationA resulting solid was collected by filtration

Sources & evidence

ORD record: ord-bfcb996fd5f84bb3a974118e1e5066f1
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476026B1

Reaction notes

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