Hydrochloric Acid → HCID 58573558, compound

HRID 1048412Notes

Reaction equation

HRID 1048412 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]([CH2:28][CH3:29])[CH2:22][C:23]([CH3:27])([CH3:26])[C:24]#[N:25])[C:11](=[O:30])[C@:10]([CH2:32][CH:33]3[CH2:37][O:36]C(C)(C)[O:34]3)([CH3:31])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl.O.[Na+].[Cl-]>C1COCC1>[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]([CH2:28][CH3:29])[CH2:22][C:23]([CH3:26])([CH3:27])[C:24]#[N:25])[C:11](=[O:30])[C@:10]([CH2:32][CH:33]([OH:34])[CH2:37][OH:36])([CH3:31])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5234Sodium ChlorideHCID 58573326HCID 58573326, compound

Product 1

HCID 58573558HCID 58573558, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4S)-4-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3-methyl-2-oxopiperidin-1-yl)-2,2-dimethylhexanenitrile prepared above in Step G (77 mg, 0.135 mmol) in THF (2.69 mL) was added 3 N hydrochloric acid in water (1.35 μL, 4.04 mmol) at rt. After being stirred at rt for 4 h, the reaction was diluted (sat. aq. NaCl) and extracted (2×EtOAc). The combined organic layers were washed (sat. aq. NaCl solution), dried (Na2SO4), and concentrated under reduced pressure to provide the title compound as a colorless foam.

Workup

  1. extractionextracted (2×EtOAc)
  2. washThe combined organic layers were washed (sat. aq. NaCl solution)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9fd751166bc34804a3a8ea3ba872c0de
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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