Diethyl Ether → HCID 86749257, compound

HRID 2396442Notes

Reaction equation

HRID 2396442 reaction equation
C([O:4][C:5]([C:7]1[N:8]2[C@H:11]([S:12][C:13]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C@@H:10]([C@H:20]([OH:22])[CH3:21])[C:9]2=[O:23])=[O:6])C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[K+:53].C(OCC)C>C(Cl)Cl.O1CCCC1>[OH:22][C@@H:20]([C@H:10]1[C:9](=[O:23])[N:8]2[C@@H:11]1[S:12][C:13]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=[C:7]2[C:5]([O-:6])=[O:4])[CH3:21].[K+:53]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 14722138HCID 14722138, compoundHCID 23669619Potassium 2-ethylhexanoate

Product 1

HCID 86749257HCID 86749257, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (332.4 g) was dissolved in a mixture of methylene chloride (2.5 liters) and tetrahydrofuran (1.3 liters). To the solution were added triphenylphosphine (26.2 g) and tetrakis(tripheylphosphine)palladium (11.6 g), followed by further addition of the above solution of potassium 2-ethylhexanoate. The mixture was stirred for 15 minutes and ethyl ether was added dropwise thereto to deposit crystals. After stirring for 30 minutes, the crystals were corrected by filtration and washed with ethyl ether (2 liters). The crystals were dried under reduced pressure to obtain crude crystals of potassium (+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.

Workup

  1. stirringAfter stirring for 30 minutes
  2. filtrationthe crystals were corrected by filtration
  3. washwashed with ethyl ether (2 liters)
  4. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-e4710d37c10145ae8b402bb5627aae32
Source dataset
uspto-grants-1996_02
Patent number
US05492903

Reaction notes

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