Sodium Hydroxide → {9-[(3-Trifluoromethoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid

HRID 51431Notes

Reaction equation

[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([O:24][CH2:25][C:26]([O:28]C)=[O:27])[C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][C:16]=3[C:30](=[O:32])[NH2:31])[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+]>C(O)C>[F:33][C:2]([F:1])([F:34])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([O:24][CH2:25][C:26]([OH:28])=[O:27])[C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][C:16]=3[C:30](=[O:32])[NH2:31])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of the {9-[(3-trifluoromethoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester (22.4 mg, 0.047 mM) and 0.065 mL (0.065 mM) of 1 N NaOH in 5 mL of ethanol was stirred for 24 hours at 25° C. The solvent was removed in vacuo and the residue suspended in EtOH. The resultant white precipitate was collected by filtration, washed with a small amount of EtOH, then dried in vacuo to afford 9 mg (41%) of the {9-[(3-trifluoromethoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, sodium salt as a white powder. MS (ES) m/e 457, 459.

Workup

customThe solvent was removed in vacuo
filtrationThe resultant white precipitate was collected by filtration
washwashed with a small amount of EtOH
customdried in vacuo

Sources & evidence

ORD record: ord-15efe6597692447596a0dde14a865850
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713645B1

Reaction notes

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