Acetic Acid → HCID 54429917, compound

HRID 620799Notes

Reaction equation

HRID 620799 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][NH:42][C:43]([NH2:45])=[O:44])=[O:6])[CH:2]=[CH2:3].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>O1CCCC1.O.C(OCC)(=O)C>[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][NH:42][C:43]([NH2:45])=[O:44])=[O:6])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 53827466HCID 53827466, compound

Product 1

HCID 54429917HCID 54429917, compoundYield 44.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-{(2-ureidoethyl)oxymethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.46 g) in tetrahydrofuran (10 ml) were added dropwise acetic acid (0.5 ml) and a 1.1 M solution (3.2 ml) of tetrabutylammonium fluoride in tetrahydrofuran at ambient temperature. The mixture was stirred at the same temperature for 26 hours. To the mixture was added ethyl acetate (100 ml) and water (100 ml). The aqueous layer was adjusted to pH 7 with saturated aqueous sodium hydrogen carbonate. The organic layer was washed with brine, dried over medium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (10 g) and eluted with a mixture of acetone and dichloromethane (2:1 V/V) to give allyl (4R,5S,6S)-3-[(2S, 4S)-1-allyloxycarbonyl-2-{(2-ureidoethyl)oxymethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.17 g).

Workup

  1. customat ambient temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried over medium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of acetone and dichloromethane (2:1 V/V)

Sources & evidence

ORD record
ord-4ff64ac09b784c4db5c1d072b422aaa9
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

Loading…