HCID 485761, compound → HCID 20658369, compound

HRID 1979279Notes

Reaction equation

HRID 1979279 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([NH:10][CH2:11][C@@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[CH:22][C:21]([S:24][CH2:25][CH2:26][OH:27])=[C:20]([F:28])[CH:19]=2)[CH2:13]1)(=[O:9])[CH3:8]>O.CO>[C:7]([NH:10][CH2:11][C@@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH2:25][CH2:26][OH:27])=[O:2])=[C:20]([F:28])[CH:19]=2)[CH2:13]1)(=[O:9])[CH3:8]

Participants

5

Reactant 2

HCID 485761HCID 485761, compoundHCID 23667635Sodium periodate

Product 1

HCID 20658369HCID 20658369, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium periodate (0.014 g, 0.065 mmol) in water (0.5 mL) was added to 5-(S)-acetamidomethyl-3-[4′-(2″-hydroxyethyl)thio-3′-fluorophenyl]-oxazo-lidine-2-one (0.020 g, 0.061 mmol) in methanol (1 mL), and the mixture was stirred at r.t. overnight. Solvent was removed under vacuum, and the residue dissolved in ethyl acetate (ca. 5 mL). Resulting solution was washed with water, brine, and dried (MgSO4). Solvent was removed under vacuum, and the crude product purified by TLC (eluent: 10% methanol in dichloromethane). Yield 0.018 g (86%). MS (m/z): 345 [M+H]+. 1H NMR.

Workup

  1. customSolvent was removed under vacuum
  2. dissolutionthe residue dissolved in ethyl acetate (ca. 5 mL)
  3. washResulting solution was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed under vacuum
  6. customthe crude product purified by TLC (eluent: 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-486c2cc6904e45a8851a91748315017b
Source dataset
uspto-grants-2001_05
Patent number
US06239152B1

Reaction notes

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