Acetic Acid → HCID 86596171, compound

HRID 1271103Notes

Reaction equation

HRID 1271103 reaction equation
[O:1]=[C:2]1[N:8]2[C@H:4]([CH2:5][C:6]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][Si](CC)(CC)CC)[CH:16]=3)=[C:7]2[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C@H:3]1[C@H:30]([O:32][Si:33]([CH2:38][CH3:39])([CH2:36][CH3:37])[CH2:34][CH3:35])[CH3:31].O.C(O)(=O)C.C(=O)([O-])O.[Na+]>C1COCC1>[OH:22][CH2:21][C:17]1[CH:16]=[C:15]([C:6]2[CH2:5][C@H:4]3[N:8]([C:2](=[O:1])[C@@H:3]3[C@H:30]([O:32][Si:33]([CH2:36][CH3:37])([CH2:34][CH3:35])[CH2:38][CH3:39])[CH3:31])[C:7]=2[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 86596170HCID 86596170, compound

Product 1

HCID 86596171HCID 86596171, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Allyl (5R,6S)-7-oxo-6-{(1R)-1-[(triethylsilyl)oxy]ethyl}-3-(3-{[(triethylsilyl)oxy]methyl}phenyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (911 mg) prepared by step b) of example 4 was dissolved in THF (13 ml), and thereto water (6 ml) and acetic acid (3 ml) were added at 0° C. After stirring for 30 minutes, a saturated aqueous sodium hydrogencarbonate solution was added thereto and the solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give allyl (5R,6S)-3-[3-(hydroxymethyl)phenyl]-7-oxo-6-{(1R)-1-[(triethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (535 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-217d105a32064d20a5369ad6b2699868
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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