Ethanol → 4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 703606Notes

Reaction equation

HRID 703606 reaction equation
C(OC(N1C[C@@H](S[C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H](O)C)[C:14]=2[C:25]([O:27]CC=C)=[O:26])C[C@H]1COCCF)=O)C=C.N1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCCC1>[CH3:20][CH:19]1[CH:18]2[N:15]([C:16](=[O:24])[CH2:17]2)[C:14]([C:25]([OH:27])=[O:26])=[CH:13]1

Participants

8

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 11776TriphenylphosphineHCID 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-carboxylate

Product 1

HCID 178370354-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidYield 87.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) [0.32 g) was added to a solution of 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 (2.35 g), morpholine (0.84 ml) and triphenylphosphine (0.24 g) in a mixture of water (3 ml), ethanol (12 ml) and tetrahydrofuran (35 ml) at ambient temperature in a stream of nitrogen, and the mixture was stirred at the same condition for 2 hours to give precipitates. The precipitates were collected by filtration, washed with tetrahydrofuran, and dried over phosphorus pentoxide to give (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)1-hydroxyethyl[-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.67 g).

Workup

  1. customto give
  2. customprecipitates
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with tetrahydrofuran
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-00f3ec74c16c40cc9c5026fee3c6d919
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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