Hydrochloric Acid → HCID 86660243, compound

HRID 1890711Notes

Reaction equation

HRID 1890711 reaction equation
C([S@@]([NH:7][C@H:8]([C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=1)[CH2:9][CH2:10][C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)(C)(C)C.Cl>CO>[NH2:7][C@H:8]([C:19]1[CH:20]=[C:21]([F:26])[CH:22]=[C:23]([F:25])[CH:24]=1)[CH2:9][CH2:10][C:11]([CH3:17])([CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86660244HCID 86660244, compound

Product 1

HCID 86660243HCID 86660243, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (5S)-5-{[(S)-tert-butylsulfinyl]amino}-5-(3,5-difluorophenyl)-2,2-dimethylpentanoate (113 mg, 0.289 mmol, prepared by direct analogy to the methyl ester version according to U.S. Patent Application Publication No. US 2007/0265225) in MeOH (6 mL), cooled to 0° C., was added excess anhydrous, gaseous HCl over 1 minute via a rapid stream of bubbles. After 30 min, a stream of nitrogen was passed over the solution to remove some HCl. The reaction was then concentrated in vacuo. The residue was diluted with DCM (20 mL) and washed with saturated sodium bicarbonate (10 mL). The bicarbonate layer was subsequently extracted twice with DCM (10 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo, to yield a residue, containing about 30% methyl ester, which was used without further purification. MS: m/z=286 (M+1).

Workup

  1. additionwas added excess anhydrous
  2. customto remove some HCl
  3. concentrationThe reaction was then concentrated in vacuo
  4. additionThe residue was diluted with DCM (20 mL)
  5. washwashed with saturated sodium bicarbonate (10 mL)
  6. extractionThe bicarbonate layer was subsequently extracted twice with DCM (10 mL)
  7. dry with materialThe combined organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a residue
  11. customwas used without further purification

Sources & evidence

ORD record
ord-96fb433e9afa47f39c63edd3174f0b16
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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