Triethylamine → HCID 86706749, compound

HRID 710036Notes

Reaction equation

HRID 710036 reaction equation
CCOC(C)=O.[F:7][C:8]([F:34])([C:23]1([OH:33])[CH2:28][C:27]([CH3:30])([CH3:29])[CH2:26][C:25]([CH3:32])([CH3:31])[CH2:24]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[CH:20]=[C:19]([CH2:21][OH:22])[O:18][N:17]=1)=[O:10].CCN(CC)CC.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>O>[CH3:42][S:43]([O:22][CH2:21][C:19]1[O:18][N:17]=[C:16]([C@@H:12]2[CH2:13][CH2:14][CH2:15][N:11]2[C:9](=[O:10])[C:8]([F:7])([F:34])[C:23]2([OH:33])[CH2:24][C:25]([CH3:32])([CH3:31])[CH2:26][C:27]([CH3:30])([CH3:29])[CH2:28]2)[CH:20]=1)(=[O:45])=[O:44]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chloride2×HCID 86706747(S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-(hydroxymethyl)isoxazol-3-yl)pyrrolidin-1-yl)ethanone

Product 1

HCID 86706749HCID 86706749, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an AcOEt (3 mL) solution of the compound (45 mg) obtained in Example 3-(4) and Et3N (31 μL), MsCl (13 μL) was added at 0° C. and after stirring the mixture for 30 minutes, MsCl (13 μL) was added and the mixture was stirred at 0° C. for 30 minutes, followed by addition of Et3N (31 μL) and stirring at 0° C. for 2.5 hours. The reaction mixture was added to water (50 mL) and the organic layer extracted with AcOEt (50 mL) was dried (MgSO4), filtered and concentrated to give the titled compound (58 mg, colorless oil.)

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes
  2. stirringstirring at 0° C. for 2.5 hours
  3. extractionthe organic layer extracted with AcOEt (50 mL)
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3eb44b70f7854e7081166ab2b5d42f8f
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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