Diethyl Ether → HCID 59922987, compound

HRID 2296608Notes

Reaction equation

HRID 2296608 reaction equation
[CH:1](=[C:3]1/[C@@H:4]2[N:12]([C:13]/1=[O:14])[C:11]([C:15]([O:17]CC=C)=[O:16])=[C:10]1[C@@H:5]2[CH2:6][CH2:7][CH2:8][CH2:9]1)/[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+:50].C(OCC)C>O1CCCC1.ClCCl.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>[CH:1](=[C:3]1/[C@@H:4]2[N:12]([C:13]/1=[O:14])[C:11]([C:15]([O-:17])=[O:16])=[C:10]1[C@@H:5]2[CH2:6][CH2:7][CH2:8][CH2:9]1)/[CH3:2].[Na+:50]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 59922993HCID 59922993, compound

Product 1

HCID 59922987HCID 59922987, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21919333Tetrahydrofurane dichloromethaneSolvent2×

Procedure

Allyl (8S,9R)-10-((E)-ethylidene)-11-oxo-1-azatricyclo-[7.2.0.03,8]undec-2-ene-2-carboxylate (73 mg; 0.267 mmole) prepared according to the process disclosed in Example 11a was dissolved in a mixture (0.5 ml) of tetrahydrofuran/dichloromethane 1:1 (v/v). To the obtained mixture there were added first a solution of triphenylphosphine (24 mg; 0.08 mmole) and then a solution of sodium 2-ethylhexanoate (46.8 mg; 0.28 mmole) and tetrakis(triphenylphosphine)palladium(0) (32 mg; 0.024 mmole) (prepared according to the process disclosed in D. R.Coulson, Inorganic Synthesis 13, 121 (1972)) in a mixture (2 ml) of tetrahydrofuran/dichloromethane (1:1). The obtained solution was stirred for 30 minutes at room temperature. To the obtained mixture diethyl ether (4 ml) was added and it was cooled to the temperature of 0° C. The separated product was filtered off, washed with an anhydrous mixture of diethyl ether/tetrahydrofuran and dried in vacuo. The title compound (32 mg; 47%) was obtained in the form of brownish crystals and with m.p. 222-225° C. with decomposition (DMF-diethyl ether).

Workup

  1. temperatureit was cooled to the temperature of 0° C
  2. filtrationThe separated product was filtered off
  3. washwashed with an anhydrous mixture of diethyl ether/tetrahydrofuran
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bcfd42ff14d84782a180cc82ed0468d2
Source dataset
uspto-grants-2002_12
Patent number
US06489318B1

Reaction notes

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