Hydrochloric Acid → HCID 57889961, compound

HRID 1820275Notes

Reaction equation

HRID 1820275 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:33])[CH2:13][CH2:12][N:11]([C:14](=[O:30])[C@H:15]([NH:19][C:20]3[S:21][CH:22]=[C:23]([CH2:25][C:26]([O:28]C)=[O:27])[N:24]=3)[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:32])[CH3:31])=[CH:4][CH:3]=1.Cl>[OH-].[Na+].C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:33])[CH2:13][CH2:12][N:11]([C:14](=[O:30])[C@H:15]([NH:19][C:20]3[S:21][CH:22]=[C:23]([CH2:25][C:26]([OH:28])=[O:27])[N:24]=3)[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:31])[CH3:32])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57889464HCID 57889464, compound

Product 1

HCID 57889961HCID 57889961, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 2-(2-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylamino)thiazol-4-yl)acetate (Example 520, 356 mg, 0.895 mmol) was stirred overnight in 1 N sodium hydroxide (2 mL) and ethanol (15 mL). The reaction was neutralized to pH 7 with 0.1N hydrochloric acid and the product was extracted with EtOAc:MeOH 95:5. The organic extracts were dried over sodium sulfate, filtered, and concentrated to yield the title compound (180 mg) which was used without further purification.

Workup

  1. extractionthe product was extracted with EtOAc:MeOH 95:5
  2. dry with materialThe organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-058447f4b2374ae0998e1997810f9d75
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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