2,2-Dimethoxypropane → HCID 67999319, compound

HRID 932095Notes

Reaction equation

HRID 932095 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:26][CH3:27])[C:22]([O:24][CH3:25])=[O:23])[C:11](=[O:28])[C@:10]([CH2:30][CH:31]([OH:34])[CH2:32][OH:33])([CH3:29])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.O.[C:36]1(C)[CH:41]=CC(S(O)(=O)=O)=C[CH:37]=1.COC(OC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[N:12]([C@@H:21]([CH2:26][CH3:27])[C:22]([O:24][CH3:25])=[O:23])[C:11](=[O:28])[C@:10]([CH2:30][CH:31]3[CH2:32][O:33][C:36]([CH3:41])([CH3:37])[O:34]3)([CH3:29])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 67999558HCID 67999558, compound

Product 1

HCID 67999319HCID 67999319, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(2,3-dihydroxypropyl)-3-methyl-2-oxopiperidin-1-yl)butanoate prepared above in Step A (749 mg, 1.47 mmol) in DCM (8.2 mL) was added p-toluenesulfonic acid monohydrate (14.0 mg, 0.074 mmol) and 2,2-dimethoxypropane (8.15 mL, 66.3 mmol). After being stirred at rt for 3 h, the reaction mixture was concentrated under reduced pressure and the residue was dissolved (EtOAc and sat. aq. NaHCO3) and extracted (3×EtOAc). The combined organic layers were washed (sat. aq. NaCl solution), dried (Na2SO4), and concentrated under reduced pressure. Purification by chromatography on silica gel (SiO2, 40 g, 27% and 37% EtOAc/Hexanes) provided the title compound as a colorless film.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved (EtOAc and sat. aq. NaHCO3)
  3. extractionextracted (3×EtOAc)
  4. washThe combined organic layers were washed (sat. aq. NaCl solution)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography on silica gel (SiO2, 40 g, 27% and 37% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-863e1f4ce0cd440392de355ac0ed30d5
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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