Hydrochloric Acid → HCID 57889961, compound

HRID 1016205Notes

Reaction equation

HRID 1016205 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-f23d5721634e4048bc960819e09e943a
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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