Ethanol → FR-27743

HRID 703608Notes

Reaction equation

HRID 703608 reaction equation
C(OC([O:7][C@@H:8]([C@H:10]1[C:16](=[O:17])[N:15]2[C@@H:11]1[C@@H:12]([CH3:41])[C:13]([S:24][C@@H:25]1[CH2:29][N:28](C(OCC=C)=O)[C@H:27]([CH2:36][O:37][CH2:38][CH2:39][F:40])[CH2:26]1)=[C:14]2[C:18]([O:20]CC=C)=[O:19])[CH3:9])=O)C=C.C(O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCOCC1>O1CCCC1.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.O.C(OCC)(=O)C>[F:40][CH2:39][CH2:38][O:37][CH2:36][C@@H:27]1[CH2:26][C@H:25]([S:24][C:13]2[C@H:12]([CH3:41])[C@H:11]3[N:15]([C:16](=[O:17])[C@@H:10]3[C@H:8]([OH:7])[CH3:9])[C:14]=2[C:18]([OH:20])=[O:19])[CH2:29][NH:28]1

Participants

9

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 11776TriphenylphosphineHCID 57317662allyl (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

Product 1

HCID 86744488FR-27743Yield 8.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 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 (372 mg) in a mixture of tetrahydrofuran (3.2 ml), ethanol (1.6 ml) and water (800 μl) were added triphenylphosphine (17 mg), morpholine (216 μl) and tetrakis(triphenylphosphine)palladium(0) (72 mg) at room temperature for 3 hours under nitrogen atmosphere. The reaction mixture was poured into a mixture of ethyl acetate (40 ml) and water (20 ml). The aqueous layer was separated and concentrated in vacuo to give a residual solution, which was chromatographed on "Diaion HP-20" eluting in turn with water and 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 (20 mg).

Workup

  1. customThe aqueous layer was separated
  2. concentrationconcentrated in vacuo
  3. customto give a residual solution, which
  4. customwas chromatographed on "Diaion
  5. wash" eluting in turn with water and 10% aqueous acetone
  6. additionThe fractions containing the desired compound
  7. customwere collected

Sources & evidence

ORD record
ord-f2f0639bb5d0443b8740510cf1e6f3ae
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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