Lithium hydroxide, monohydrate → 7-(Benzyloxycarbonylamino)-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 2361260Notes

Reaction equation

HRID 2361260 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])=[CH:23][N:22]=[C:21]([C:32]([O:34]CC)=[O:33])[C:17]=3[NH:18]2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])=[CH:23][N:22]=[C:21]([C:32]([OH:34])=[O:33])[C:17]=3[NH:18]2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67994853Ethyl 7-(benzyloxycarbonylamino)-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 679951827-(Benzyloxycarbonylamino)-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxylic acidYield 95.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-(benzyloxycarbonylamino)-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxylate (0.238 g, 0.492 mmol) in tetrahydrofuran (12 mL) and methanol (4 mL) at room temperature was added a solution of lithium hydroxide hydrate (0.083 g, 1.969 mmol) in water (1.8 mL). The mixture was stirred at room temperature for 1 hr, and then concentrated under vacuum. To the residue was added water (5 ml), and the mixture was acidified to pH 5 with 1 N HCl. The precipitating product (0.214 g, 0.470 mmol, 95% yield) was collected by suction filtration and dried over Drierite under vacuum.

Workup

  1. concentrationconcentrated under vacuum
  2. additionTo the residue was added water (5 ml)

Sources & evidence

ORD record
ord-3b5a3addb413464cac367a62ef5c4e6a
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…