Ammonium Chloride → 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic Acid

HRID 2274108Notes

Reaction equation

[C:1]([CH2:4][C:5]1(C([O-])=O)[C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([CH:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)=[C:21]([C:30]([F:33])([F:32])[F:31])[CH:20]=4)=[CH:15][C:16]=3[C:8]=2[CH2:7][CH2:6]1)([O-:3])=[O:2].[Na+].[Na+].[Cl-].[NH4+]>O>[CH:25]1([C:22]2[CH:23]=[CH:24][C:19]([CH2:18][O:17][C:14]3[CH:13]=[CH:12][C:11]4[NH:10][C:9]5[CH:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:6][CH2:7][C:8]=5[C:16]=4[CH:15]=3)=[CH:20][C:21]=2[C:30]([F:33])([F:31])[F:32])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 92 °C

Procedure

To a stirred solution of sodium 3-(carboxylatomethyl)-7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indole-3-carboxylate (16.5 g, 30.2 mmol) in water at 40° C. was added ammonium chloride solution (9.71%, 100 mL). The reaction was heated at 92° C. (bath) for 4.4 h. The mixture was refrigerated overnight, decanted and triturated with ice cold 6N HCl (100 mL). The solid was collected by filtration, washed with diluted HCl (100 mL) and dried overnight in a vacuum oven at 40° C. to give the title compound (8.5 g). LCMS m/z=458.3 [M+H]+.

Workup

customdecanted
customtriturated with ice cold 6N HCl (100 mL)
filtrationThe solid was collected by filtration
washwashed with diluted HCl (100 mL)
customdried overnight in a vacuum oven at 40° C.

Sources & evidence

ORD record: ord-ede6859e39544364b92548d29b331174
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126932B2

Reaction notes

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