1-(Triphenylphosphoranylidene)acetone → HCID 70616394, compound

HRID 2420575Notes

Reaction equation

HRID 2420575 reaction equation
[CH:1]([C:3]1[CH:8]([C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[N:7]2[C:25](=[O:36])[C@@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C@H:6]2[S:5][CH:4]=1)=O.[CH3:37][C:38]([CH:40]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:39]>C1C=CC=CC=1>[CH3:37][C:38](/[CH:40]=[CH:1]/[C:3]1[CH:8]([C:9]([O:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:10])[N:7]2[C:25](=[O:36])[C@@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C@H:6]2[S:5][CH:4]=1)=[O:39]

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 88793624HCID 88793624, compound

Product 1

HCID 70616394HCID 70616394, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of diphenylmethyl 3-formyl-7β-(2-thienylacetamido)ceph-2-em-4-carboxylate (116 mg.) in benzene (3 ml.) was treated with a solution of methylcarbonylmethylenetriphenylphosphorane (150 mg.) in benzene (4 ml.) and the mixture refluxed for 5.75 hours. The organic solution was washed with 2-N-hydrochloric acid and water, dried and evaporated in vacuo. The residual gum (186 mg.) was purified by preparative T.L.C. (Kieselgel HF254+366, developed five times with benzene-ethyl acetate = 8:1) to give the title compound (32 mg, 27%) as a gum, λmax. (CHCl3) 318 nm. (qualitative, τ (CDCl3) 3.00 and 3.86 (CH=CH, two d, J 16 Hz), 3.12 (CHPh2), 3.27 (C(2) -H, broad s), 4.47 (C(7) -H), dd, J 8 and 4 Hz), 4.73 (C(6) -H, d, J 4 Hz), 4.69 (C(4) -H, broad s), 6.16 (CH 2 CONH) and 7.91 (COCH3).

Workup

  1. temperaturethe mixture refluxed for 5.75 hours
  2. washThe organic solution was washed with 2-N-hydrochloric acid and water
  3. customdried
  4. customevaporated in vacuo
  5. customThe residual gum (186 mg.) was purified by preparative T.L.C

Sources & evidence

ORD record
ord-37f04708b9cf42c99b827c49baf5745e
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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