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

HRID 2361361Notes

Reaction equation

HRID 2361361 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:37])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([Br:31])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:32]([O:34]CC)=[O:33])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=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[C:13]([CH3:37])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([Br:31])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:32]([OH:34])=[O:33])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=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 67994617Ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 679946604-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxylic acidYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxylate (1.338 g, 2.396 mmol) in tetrahydrofuran (48 mL) and methanol (16 mL) at room temperature was added a solution of lithium hydroxide hydrate (0.402 g, 9.58 mmol) in water (10 mL). The resulting solution was stirred at room temperature for 1.5 hr, and then concentrated under vacuum to a volume of about 10 mL. The residue was diluted with water (5 mL) and neutralized with 1 N HCl solution to pH 5-6. The precipitating product (1.177 g, 2.219 mmol, 93% yield) was collected as a beige solid by suction filtration and dried over Drierite under vacuum.

Workup

  1. concentrationconcentrated under vacuum to a volume of about 10 mL
  2. additionThe residue was diluted with water (5 mL)

Sources & evidence

ORD record
ord-5b6c2ec5cf26463aa9b19f75ecfa559f
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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