Hydrochloric Acid → HCID 86709299, compound

HRID 2205568Notes

Reaction equation

HRID 2205568 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][CH2:22][C:21]=3[C:28]3[CH:29]=[C:30]([C:36]4[CH2:41][CH2:40][CH:39]([C:42]([O:44]C)=[O:43])[CH2:38][CH:37]=4)[CH:31]=[CH:32][C:33]=3[O:34][CH3:35])[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Li+].Cl>O1CCOCC1.O.CCOC(C)=O>[F:48][C:2]([F:1])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][CH2:22][C:21]=3[C:28]3[CH:29]=[C:30]([C:36]4[CH2:41][CH2:40][CH:39]([C:42]([OH:44])=[O:43])[CH2:38][CH:37]=4)[CH:31]=[CH:32][C:33]=3[O:34][CH3:35])[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86709300HCID 86709300, compound

Product 1

HCID 86709299HCID 86709299, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

According to the same method as the synthesis of Compound 354, the obtained methyl 4-(3-(2-(((4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyl-2-oxooxazolidin-3-yl)methyl)-4,4-dimethylcyclohex-1-enyl)-4-methoxyphenyl)cyclohex-3-enecarboxylate was dissolved in dioxan/water (5 mL, v/v 2:1). Lithium hydroxide (10 mg) was added dropwise to the obtained solution at room temperature, and stirred at room temperature for 5 hours. After the completion of the reaction, the reaction mixture was acidified with 2 M HCl solution. The reaction mixture was diluted with EtOAc, was washed with water and brine. The organic layers were collected, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to remove the solvent. The residue was separated by MPLC (3:1 hexane:EtOAc), thus obtaining Compound 362 (30 mg, 24%) as white solid foam.

Workup

  1. customAfter the completion of the reaction
  2. washwas washed with water and brine
  3. customThe organic layers were collected
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto remove the solvent
  8. customThe residue was separated by MPLC (3:1 hexane:EtOAc), thus obtaining Compound 362 (30 mg, 24%) as white solid foam

Sources & evidence

ORD record
ord-473284647bb5428e83e7a931bca1e57b
Source dataset
uspto-grants-2016_06
Patent number
US09371294B2

Reaction notes

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