Hydrochloric Acid → HCID 76445789, compound

HRID 533557Notes

Reaction equation

HRID 533557 reaction equation
[CH3:1][C:2]([S:28]([CH3:31])(=[O:30])=[O:29])([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl.CO>C(Cl)Cl>[OH:6][NH:5][C:3](=[O:4])[C:2]([CH3:1])([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86668774HCID 86668774, compound

Product 1

HCID 76445789HCID 76445789, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-2-(methylsulfonyl)-4-[4-(phenylthio)phenyl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (268.4 mg, 0.579 mmol) in methylene chloride (3 mL) at ambient temperature was added HCl (4M in 1,4-dioxane, 4.34 mL, 17.4 mmol) and the resulting solution was stirred at RT for 5 minutes. Methanol (500 uL) was added followed by silica gel and the mixture was concentrated to dryness. The crude material was purified via silica gel chromatography eluting with methylene chloride/methanol to afford N-hydroxy-2-methyl-2-(methylsulfonyl)-4-[4-(phenylthio)phenyl]butanamide as a solid. 7.8 mg. LCMS: (M+1) 380.1.

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. customThe crude material was purified via silica gel chromatography
  3. washeluting with methylene chloride/methanol

Sources & evidence

ORD record
ord-12368b6876c54bb6b73e411be41c7faf
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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