Hydrochloric Acid → 2-hydroxy-3-methyl-2-[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1.5]benzodiazepin-8-yl]butanoic acid

HRID 1691474Notes

Reaction equation

HRID 1691474 reaction equation
[OH:1][C:2]([C:11]1[CH:12]=[CH:13][C:14]2[NH:20][C:19]3[N:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:18]=3[CH2:17][N:16]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:15]=2[CH:43]=1)([CH:8]([CH3:10])[CH3:9])[C:3]([O:5]CC)=[O:4].[Li+].[OH-].Cl>CCO.O>[OH:1][C:2]([C:11]1[CH:12]=[CH:13][C:14]2[NH:20][C:19]3[N:21]=[C:22]([C:25]([F:27])([F:28])[F:26])[CH:23]=[CH:24][C:18]=3[CH2:17][N:16]([S:29]([C:32]3[CH:33]=[CH:34][C:35]([O:38][C:39]([F:40])([F:42])[F:41])=[CH:36][CH:37]=3)(=[O:31])=[O:30])[C:15]=2[CH:43]=1)([CH:8]([CH3:10])[CH3:9])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59618714Ethyl 2-hydroxy-3-methyl-2-[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]butanoate

Product 1

HCID 596187012-hydroxy-3-methyl-2-[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1.5]benzodiazepin-8-yl]butanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-hydroxy-3-methyl-2-[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]butanoate (153 mg, 0.242 mmol, Example 509) in 4 mL of EtOH was added a solution of 1N LiOH (2.5 ml) in water, and the solution was stirred for 48 h at rt. LC-MS showed the reaction complete. The reaction pH was adjusted to 6-7 with 1N HCl, and the mixture was concentrated. The resulting residue was dissolved in CH2Cl2 and filtered to remove the salt. The filtrate was concentrated and the residue was purified by chromatography to give the title compound as a white solid; Mass Spectrum: m/e=606 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe resulting residue was dissolved in CH2Cl2
  3. filtrationfiltered
  4. customto remove the salt
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-994ecc355445497595bf6acac1c7b605
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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