Lithium Hydroxide → HCID 59487243, compound

HRID 570673Notes

Reaction equation

HRID 570673 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH2:11][CH:12]([N:15]3[C:19]([CH3:20])=[C:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[N:17]=[N:16]3)[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:29][C:30]([O:32]CC)=[O:31].[Li+].[OH-]>C1COCC1.CO.O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH2:11][CH:12]([N:15]3[C:19]([CH3:20])=[C:18]([CH2:21][C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[N:17]=[N:16]3)[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:29][C:30]([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 123394588HCID 123394588, compound

Product 1

HCID 59487243HCID 59487243, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The racemic ethyl {4-fluoro-7-[4-(4-fluorobenzyl)-5-methyl-1H-1,2,3-triazol-1-yl]-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl}acetate (as described in Example 36) was hydrolyzed to the final acid product by dissolving in 1:1:1 THF/MeOH/water (0.06 M), treating with LiOH (3.6 eq.) and stirring overnight. The reaction mixture was then diluted with EtOAc, extracted with 2 N HCl, water, dried (Na2SO4), and concentrated to provide the title compound: MS (EI) calc'd for C24H23F2N4O2 [M+1]+437.2, found 437.1.

Workup

  1. extractionextracted with 2 N HCl, water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d0183a2b8f574d5ebe330f14f07ce7ba
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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