Lithium hydroxide, monohydrate → HCID 67994548, compound

HRID 2361320Notes

Reaction equation

HRID 2361320 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:46])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([NH:31][C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[O:33])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:41]([O:43]CC)=[O:42])=[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]([CH3:46])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([NH:31][C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:38])([CH3:39])[CH3:40])=[O:33])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:41]([OH:43])=[O:42])=[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 67994641HCID 67994641, compound

Product 1

HCID 67994548HCID 67994548, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a homogeneous, burgundy solution of ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-((2-(trimethylsilyl)ethoxy)carbonylamino)-9H-pyrido[3,4-b]indole-1-carboxylate (0.565 g, 0.884 mmol) in tetrahydrofuran (30.2 mL) and methanol (10.05 mL) was added a solution of lithium hydroxide hydrate (0.148 g, 3.54 mmol) in water (4 mL). After 1 hr, the reaction was concentrated in vacuo, acidified with 1 N aqueous HCl to pH ˜5 by litmus paper. The precipitate was filtered, dried over Drierite to give the desired product (0.419 g, 0.686 mmol, 78% yield) as a light brown solid.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. filtrationThe precipitate was filtered
  3. dry with materialdried over Drierite

Sources & evidence

ORD record
ord-6fcc8c3bb30548e181caa86a0b2107d1
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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