Potassium Carbonate → HCID 58573186, compound

HRID 932124Notes

Reaction equation

HRID 932124 reaction equation
[CH2:1]([C@@:4]1([CH3:36])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([CH:24]([CH2:33][CH3:34])[C:25]([NH:27][C:28]([CH3:32])([CH3:31])[CH2:29]O)=[O:26])[C:5]1=[O:35])[CH:2]=[CH2:3].C(N(S(F)(F)F)CC)C.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([C@@:4]1([CH3:36])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@H:24]([C:25]2[O:26][CH2:32][C:28]([CH3:31])([CH3:29])[N:27]=2)[CH2:33][CH3:34])[C:5]1=[O:35])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 58573554HCID 58573554, compound

Product 1

HCID 58573186HCID 58573186, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (-78° C.) solution of 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)-N-(1-hydroxy-2-methylpropan-2-yl)butanamide (89 mg, 0.167 mmol; Example 179, Step A: epimeric mixture) in DCM (1674 μL) was added 3 eq. of diethylaminosulfur trifluoride (26.5 μL, 0.201 mmol) dropwise. The reaction mixture was stirred at −78° C. for 20 min. Anhydrous K2CO3 (1.5 equiv) was then added in one portion and the mixture was allowed to warm to ambient temperature. The reaction was poured into saturated aqueous NaHCO3, and the biphasic mixture was extracted with EtOAc×2. The combined organic extracts were dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (eluent: 0 to 20% ethyl acetate/hexane) provided the title compound.

Workup

  1. temperatureto warm to ambient temperature
  2. extractionthe biphasic mixture was extracted with EtOAc×2
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification of the residue by flash chromatography on silica gel (eluent: 0 to 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1b574994a54e42639d8fbe12185967c4
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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