HCID 131715512, compound → HCID 131715511, compound

HRID 1252209Notes

Reaction equation

HRID 1252209 reaction equation
COC1C=CC(C[O:8][C:9]([C:11]2[CH:57]=[CH:56][C:14]([C:15]([S:17][CH:18]3[N:21]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=4)=[O:23])[C:20](=[O:35])[CH:19]3[CH:36]=[P:37]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:16])=[CH:13][CH:12]=2)=[O:10])=CC=1>FC(F)(F)C(O)=O.C(OCC)(=O)C>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([S:17][CH:18]2[N:21]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=3)=[O:23])[C:20](=[O:35])[CH:19]2[CH:36]=[P:37]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:16])=[CH:56][CH:57]=1)([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 131715512HCID 131715512, compound

Product 1

HCID 131715511HCID 131715511, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(4-p-methoxybenzyloxycarbonylbenzoylthio)-1-p-nitrobenzyloxycarbonyltriphenylphosphoranylidenemethyl-2-azetidinone (1.65 g) and anizole (0.54 g) in trifluoroacetic acid (4.1 ml) was stirred for 0.5 hour at 0° C. Evaporation of trifluoroacetic acid gave an oily residue which was dissolved in ethyl acetate. The ethyl acetate solution was extracted with aqueous potassium carbonate. The aqueous layer was washed with ether, acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give 4-(4-carboxybenzoylthio)-1-p-nitrobenzyloxycarbonyltriphenylphosphoranylidenemethyl-2-azetidinone.

Workup

  1. customEvaporation of trifluoroacetic acid
  2. customgave an oily residue which
  3. extractionThe ethyl acetate solution was extracted with aqueous potassium carbonate
  4. washThe aqueous layer was washed with ether
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-e53e67a0f64d4d9f9a3cd0a29b8c80a7
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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