Water → Fropenem

HRID 1012037Notes

Reaction equation

HRID 1012037 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[S:6][C:7]([C@H:18]1[CH2:22][CH2:21][CH2:20][O:19]1)=[C:8]2[C:12]([O:14]CC=C)=[O:13])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Na].C(C(CCCC)C([O-])=O)C.O>C(Cl)Cl.CC(C)=O>[CH3:3][C@@H:2]([OH:1])[C@H:4]1[C:10](=[O:11])[N:9]2[C:8]([C:12]([OH:14])=[O:13])=[C:7]([C@@H:18]3[O:19][CH2:20][CH2:21][CH2:22]3)[S:6][C@H:5]12

Participants

7

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 9949208Faropenem Related Compound 4HCID 131729018HCID 131729018, compound

Product 1

HCID 65894Fropenem

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

Allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (72 g, 0.221 mol) was dissolved in methylene chloride (950 ml). The solution was cooled to 10° C. and triphenyl phosphine (2.0 g, 0.0076 mol), sodium-2-ethylhexanoate (39.71 g, 0.239 mol) and tetrakis triphenylphosphine palladium (0) (2.0 g) were added together at 10° C. The reaction mixture was stirred for 1-2 hours at 10-15° C. After the completion of reaction, water (50 ml) was added to the reaction mixture. The reaction mixture was stirred for 15 minutes, followed by the addition of acetone (332.5 ml) and the reaction mixture was cooled to 0° C. The solid so separated from the reaction mixture was filtered, washed with acetone and dried under reduced pressure to obtain the title compound.

Workup

  1. additionwas added to the reaction mixture
  2. stirringThe reaction mixture was stirred for 15 minutes
  3. temperaturethe reaction mixture was cooled to 0° C
  4. customThe solid so separated from the reaction mixture
  5. filtrationwas filtered
  6. washwashed with acetone
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-e9fe6b02078a40a6bc5d803c2bbc225a
Source dataset
uspto-grants-2011_07
Patent number
US07977475B2

Reaction notes

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