Sodium Hydroxide → BMS-986020

HRID 2391055Notes

Reaction equation

HRID 2391055 reaction equation
C([O:4][C:5]([C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:26][N:25]=[C:24]([CH3:27])[C:23]=4[NH:28][C:29]([O:31][C@@H:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH3:33])=[O:30])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)=[O:6])(C)C.[OH-].[Na+]>C1COCC1.CO.O>[CH3:27][C:24]1[C:23]([NH:28][C:29]([O:31][C@@H:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH3:33])=[O:30])=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:13]3[CH:12]=[CH:11][C:10]([C:7]4([C:5]([OH:6])=[O:4])[CH2:9][CH2:8]4)=[CH:15][CH:14]=3)=[CH:17][CH:18]=2)[O:26][N:25]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66993099HCID 66993099, compound

Product 1

HCID 49792850BMS-986020Yield 72.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To the isopropyl ester from Step 7 (5.2 g, 10 mmol) in THF (30 mL), MeOH (10 mL) was added NaOH (2 g, 50 mmol) in water (10 mL). The solution is heated to 65° C. for 5 hours. The solution was cooled to room temperature, extracted with methylene chloride and dilute hydrochloric acid. The organic was dried and evaporated and the product was purified by column chromatography (0 to 60% EtOAc/hexanes) to yield ˜3.5 grams of product.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with methylene chloride and dilute hydrochloric acid
  3. customThe organic was dried
  4. customevaporated
  5. customthe product was purified by column chromatography (0 to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-af4f7df3163c4e3aa91f3c7955abbe76
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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