Ethanol → FR-27743

HRID 703609Notes

Reaction equation

HRID 703609 reaction equation
C(OC(O[C@@H]([O:10][C:11]([C:13]1[N:14]2[CH:17]([CH:18]([CH3:37])[C:19]=1[S:20][C@@H:21]1[CH2:25][N:24](C(OCC=C)=O)[C@H:23]([CH2:32][O:33][CH2:34][CH2:35][F:36])[CH2:22]1)[CH2:16][C:15]2=[O:38])=[O:12])C)=O)C=C.[CH2:39]([OH:41])[CH3:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)CC(=O)CC(=O)C1>CC(C)CC(=O)C.C(OCC)(=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>[F:36][CH2:35][CH2:34][O:33][CH2:32][C@@H:23]1[CH2:22][C@H:21]([S:20][C:19]2[C@H:18]([CH3:37])[C@H:17]3[N:14]([C:15](=[O:38])[C@@H:16]3[C@H:39]([OH:41])[CH3:40])[C:13]=2[C:11]([OH:10])=[O:12])[CH2:25][NH:24]1

Participants

9

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 31358DimedoneHCID 86744494(1R)-1-allyloxycarbonyloxyethyl-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyl)oxymethylpyrrolidin-4-yl]thio-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 86744488FR-27743

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (4R,5S,6S)-6-[(1R)-1-allyloxycarbonyloxyethyl-3-[(2S,4S)-1-allyloxycarbonyl-2-(2- fluoroethyl)oxymethylpyrrolidin-4-yl]thio-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (350 mg) in a mixture of 4-methyl-2-pentanone (4.2 ml), ethanol (2.1 ml) and water (170 μl) was added triphenylphosphine (16 mg), 5,5-dimethyl-1,3-cyclohexanedione (255 mg) and tetrakis(triphenylphosphine)palladium(0) (68 mg) at room temperature for 3 hours under nitrogen atmosphere. Evaporation of the solvent gave a residue, which was dissolved in a mixture of ethyl acetate (40 ml) and water (20 ml). The aqueous layer was separated and concentrated. The residual solution was chromatographed on "Diaion HP-20" eluting with 10% aqueous acetone. The fractions containing the desired compound were collected, and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyl)oxymethylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (100 mg).

Workup

  1. customEvaporation of the solvent
  2. customgave a residue, which
  3. customThe aqueous layer was separated
  4. concentrationconcentrated
  5. customThe residual solution was chromatographed on "Diaion
  6. wash" eluting with 10% aqueous acetone
  7. additionThe fractions containing the desired compound
  8. customwere collected

Sources & evidence

ORD record
ord-8b9967c4d34b4bc599761c9a716678b9
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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