Diethyl Ether → HCID 58691113, compound

HRID 2376675Notes

Reaction equation

HRID 2376675 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:16][C@H:15]3[N:12]([C:13](=[O:20])[C@@H:14]3[C@H:17]([OH:19])[CH3:18])[C:11]=2[C:21]([O-:23])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Na+].[C:25]([O:31][CH2:32]I)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].C(OCC)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:16][C@H:15]3[N:12]([C:13](=[O:20])[C@@H:14]3[C@H:17]([OH:19])[CH3:18])[C:11]=2[C:21]([O:23][CH2:32][O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 104401Iodomethyl pivalateHCID 58691129HCID 58691129, compound

Product 1

HCID 58691113HCID 58691113, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium (5R,6S)-3-(3-fluoro-4-methoxyphenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (100 mg) in DMF (3 mL) was added at 0° C. pivaloyloxymethyl iodide (77 mg), and the mixture was stirred for 15 minutes. To the reaction mixture was added diethyl ether (50 mL), and the mixture was washed with saturated brine (50 mL×3times), dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. The residue was purified under silica gel column chromatography (chloroform:methanol=100:0˜100:3) to give [(2,2-dimethylpropanoyl)oxy]methyl (5R,6S)-3-(3-fluoro-4-methoxyphenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (70 mg, 55%).

Workup

  1. washthe mixture was washed with saturated brine (50 mL×3times)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified under silica gel column chromatography (chloroform:methanol=100:0˜100:3)

Sources & evidence

ORD record
ord-26ab339014fb4b23b471da08779eab95
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

Loading…