Acetic Acid → HCID 86744492, compound

HRID 703604Notes

Reaction equation

HRID 703604 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:31])[C@@H:17]3[C@H:21]([O:23][Si](C(C)(C)C)(C)C)[CH3:22])[C:14]=2[C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33])[CH2:9][C@H:8]1[CH2:38][O:39][CH2:40][CH2:41][Cl:42])=[O:6])[CH:2]=[CH2:3].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:31])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33])[CH2:9][C@H:8]1[CH2:38][O:39][CH2:40][CH2:41][Cl:42])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86744493HCID 86744493, compound

Product 1

HCID 86744492HCID 86744492, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-chloroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.72 g) in tetrahydrofuran (7.2 ml) were added glacial acetic acid (0.65 ml) and a 1M solution (5.6 ml) of tetrabutylammonium fluoride in tetrahydrofuran in a stream of nitrogen, and the mixture was stirred at room temperature for 10 hours. To the mixture was added ethyl acetate (50 ml). The solution was washed with water (50 ml×3), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was chromatographed on silica gel (10 g) and eluted with a mixture of hexane and ethyl acetate (80:20 V/V) to give allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-chloroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.30 g).

Workup

  1. washThe solution was washed with water (50 ml×3)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a syrup
  5. customThe syrup was chromatographed on silica gel (10 g)
  6. washeluted with a mixture of hexane and ethyl acetate (80:20 V/V)

Sources & evidence

ORD record
ord-96afce881a8c43379ef2d944729ec6ae
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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