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

HRID 2361337
Notes
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Reaction equation

HRID 2361337 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([F:41])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:36]([O:38]CC)=[O:37])=[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[Li].O>C1COCC1.CO.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([F:41])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:36]([OH:38])=[O:37])=[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67995140Ethyl 4-(3-(benzyloxycarbonylamino)-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 679948974-(3-(Benzyloxycarbonylamino)-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylic acidYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a light orange, homogeneous solution of ethyl 4-(3-(benzyloxycarbonylamino)-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylate (0.8002 g, 1.435 mmol) in THF (30.8 mL) and MeOH (10.25 mL) was added a solution of LiOH hydrate (0.241 g, 5.74 mmol) in water (2 mL). After 1.5 hr. the reaction was concentrated in vacuo. Water (10 mL) was added followed by 1 N aqueous HCl to pH 4-5 by litmus paper. The precipitate was filtered and washed with water, dried over Drierite under vacuum to give the desired product (0.705 g, 1.331 mmol, 93% yield) as a tan solid.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additionWater (10 mL) was added
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. dry with materialdried over Drierite under vacuum

Sources & evidence

ORD record
ord-ff1d8cff858e4f00b7bd88a661895e94
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08685969B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes