Water → allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 703603Notes

Reaction equation

HRID 703603 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][F:42])=[O:6])[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1.C(O)(=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][F:42])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 57089568allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 57017483allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 53.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (250 mg) in tetrahydrofuran (5 ml) were added 1M tetrabutylammonium fluoride in tetrahydrofuran (1.2 ml) and acetic acid (0.8 ml), and the solution was stirred at room temperature for 23 hours. Water (10 ml) and ethyl acetate (10 ml) were added and stirred for 5 minutes. The organic layer was separated washed with brine (10 ml), dried and evaporated to give an oily residue, which was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:1 V/V) to give allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene- 2-carboxylate (110 mg), which was identified by comparison of the infrared spectrum with that of an authentic sample. ##STR29##

Workup

  1. stirringstirred for 5 minutes
  2. customThe organic layer was separated
  3. washwashed with brine (10 ml)
  4. customdried
  5. customevaporated
  6. customto give an oily residue, which
  7. customwas chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:1 V/V)

Sources & evidence

ORD record
ord-9fae4e30c7864403a942fcdee72201cc
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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