Ethyl Acetate → HCID 90416740, compound

HRID 1777264Notes

Reaction equation

HRID 1777264 reaction equation
[CH3:1][C:2]1([CH3:27])[O:6][C@H:5]([C:7]([N:9]2[CH2:13][C@@H:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([OH:22])[CH:15]=3)[C@@:11]([C@H:24]([OH:26])[CH3:25])([CH3:23])[CH2:10]2)=[O:8])[CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH:39]1[CH2:42][N:41]([CH:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:40]1)(=O)=O.C(OCC)(=O)C>C(#N)C>[CH3:27][C:2]1([CH3:1])[O:6][C@H:5]([C:7]([N:9]2[CH2:13][C@@H:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:39]4[CH2:42][N:41]([CH:43]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)[CH2:40]4)[CH:15]=3)[C@@:11]([C@H:24]([OH:26])[CH3:25])([CH3:23])[CH2:10]2)=[O:8])[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 9999760HCID 9999760, compound

Product 1

HCID 90416740HCID 90416740, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of (1R)-1-[(3S,4S)-1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]carbonyl}-4-(4-methoxy-3-hydroxyphenyl)-3-methylpyrrolidin-3-yl]ethanol (2.0 g) and potassium carbonate (1.46 g) in acetonitrile (30 mL) is added 1-(diphenylmethyl)azetidin-3-yl methanesulfonate (2.51 g). The mixture is heated at 80° C. overnight. Cool the reaction mixture and pour into ethyl acetate (100 mL), wash with water (40 mL) and brine (40 mL), dry over sodium sulfate, filter and evaporate the filtrate to dryness. Purify the resulting residue (silica gel, 60% ethyl acetate/hexanes to ethyl acetate) to provide 0.6 g of the title compound. MS (ES+)=601 (M+1).

Workup

  1. temperatureCool the reaction mixture
  2. washwash with water (40 mL) and brine (40 mL)
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. customevaporate the filtrate to dryness
  6. customPurify the resulting residue (silica gel, 60% ethyl acetate/hexanes to ethyl acetate)

Sources & evidence

ORD record
ord-4df535d8c3f142849883abe75cb78d4e
Source dataset
uspto-grants-2016_02
Patent number
US09266859B2

Reaction notes

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