Water → sodium 4-{(1S)-1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]ethyl}benzoate

HRID 870060Notes

Reaction equation

HRID 870060 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:32])=[C:5]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[C:6]=1[C:7]([NH:9][C@H:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8].C1COCC1.O.[OH-].[Na+:40]>CCO>[CH3:1][C:2]1[S:3][C:4]([CH3:32])=[C:5]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:27]=2)[C:6]=1[C:7]([NH:9][C@H:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([O-:18])=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8].[Na+:40]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 249529274-{(1S)-1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]ethyl}benzoic acid

Product 1

HCID 24953629sodium 4-{(1S)-1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]ethyl}benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-{(1S)-1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]ethyl}benzoic acid from Example 12 (1.70 g, 3.68 mmol) in a mixture of EtOH (50 mL), THF (15 mL) and water (15 mL) was added NaOH (1N in water, 3.68 mL, 3.68 mmol). After 10 min. the solution was concentrated to dryness and the residue was dried under high vacuum to afford the desired product as an off-white solid. MS (−APCI): m/z 460 (M−23)−.

Workup

  1. concentrationAfter 10 min. the solution was concentrated to dryness
  2. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-701c4afcfa1b41f6ba4048d86cfdd87d
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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