Sodium Hydroxide → Sodium 3-(Carboxylatomethyl)-7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indole-3-carboxylate

HRID 2040595Notes

Reaction equation

[CH:1]1([C:6]2[CH:36]=[CH:35][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[NH:17][C:16]5[C:21]([CH2:29][C:30]([O:32]CC)=[O:31])([C:24]([O:26]CC)=[O:25])[CH2:22][CH2:23][C:15]=5[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:37]([F:40])([F:39])[F:38])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+:42]>C(O)(C)C>[C:30]([CH2:29][C:21]1([C:24]([O-:26])=[O:25])[C:16]2[NH:17][C:18]3[CH:19]=[CH:20][C:12]([O:11][CH2:10][C:9]4[CH:35]=[CH:36][C:6]([CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)=[C:7]([C:37]([F:38])([F:39])[F:40])[CH:8]=4)=[CH:13][C:14]=3[C:15]=2[CH2:23][CH2:22]1)([O-:32])=[O:31].[Na+:42].[Na+:42]

Participants

Conditions

Temperature: 100 °C

Procedure

In a 500 mL flask was placed ethyl 7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-3-(2-ethoxy-2-oxoethyl)-1,2,3,4-tetrahydrocyclopenta[b]indole-3-carboxylate (24.1 g, 43.2 mmol) in isopropanol (275 mL). Sodium hydroxide solution (20%, 129.5 mL, 130 mmol) was added and the mixture was heated at 100° C. (bath) for 2.5 h. The mixture was cooled, filtered, washed with isopropanol, and dried overnight under vacuum at 40° C. to give the title compound (17.5 g). LCMS m/z=502.6 [M−2Na+3H]+.

Workup

customIn a 500 mL flask was placed
temperatureThe mixture was cooled
filtrationfiltered
washwashed with isopropanol
customdried overnight under vacuum at 40° C.

Sources & evidence

ORD record: ord-3a1d4254b3094a829ee48773aa177466
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580841B2

Reaction notes

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