Sodium Hydroxide → MK-2894 (sodium salt)

HRID 870068Notes

Reaction equation

HRID 870068 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:33])=[C:5]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[C:6]=1[C:7]([NH:9][C:10]1([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].[OH-].[Na+:35]>CCO>[CH3:1][C:2]1[S:3][C:4]([CH3:33])=[C:5]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:30])[F:32])=[CH:27][CH:28]=2)[C:6]=1[C:7]([NH:9][C:10]1([C:13]2[CH:21]=[CH:20][C:16]([C:17]([O-:19])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].[Na+:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24952929MK-2894

Product 1

HCID 24953972MK-2894 (sodium salt)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-{1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic acid from Example 16, Step 4 (112 mg, 0.236 mmol) in EtOH (5 mL), was treated with NaOH (1.0N in water, 236 μL, 0.236 mmol) after which a precipitate was formed. The mixture then obtained was concentrated to dryness. Water (15 mL) was added to the residue. The very fine resulting suspension was frozen in a bath of dry ice and acetone and lyophilized to afford the desired product as a white fluffy solid. MS (−APCI): m/z 472 (M−23)−.

Workup

  1. customwas formed
  2. customThe mixture then obtained
  3. concentrationwas concentrated to dryness
  4. additionWater (15 mL) was added to the residue
  5. temperatureThe very fine resulting suspension was frozen in a bath of dry ice and acetone

Sources & evidence

ORD record
ord-3ef53e3cd02d4263bff0dd5e98e907fa
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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