Triphenylphosphine → HCID 131715980, compound

HRID 1905102Notes

Reaction equation

HRID 1905102 reaction equation
C(C(CCCC)C([O-])=O)C.[Na+:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:31]1[CH:36]=[CH:35][C:34]([S:37][C:38]2[CH2:39][C@@H:40]3[C@@H:50]([C@H:51]([OH:53])[CH3:52])[C:49](=[O:54])[N:41]3[C:42]=2[C:43]([O:45]CC=C)=[O:44])=[CH:33][CH:32]=1>C(OCC)(=O)C.ClCCl.CC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:31]1[CH:36]=[CH:35][C:34]([S:37][C:38]2[CH2:39][C@@H:40]3[C@@H:50]([C@H:51]([OH:53])[CH3:52])[C:49](=[O:54])[N:41]3[C:42]=2[C:43]([O-:45])=[O:44])=[CH:33][CH:32]=1.[Na+:11]

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 131715979HCID 131715979, compound

Product 1

HCID 131715980HCID 131715980, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.8 ml (1.4 mmol - 1.05 equivalents) of 0.5 M sodium 2-ethylhexanoate in ethyl acetate, 35 mg (0.13 mmol - 0.1 equivalent) of triphenylphosphine and 35 mg (0.03 mmol) of tetrakis-(triphenylphosphine)-palladium (0) were successively added to a solution of 462 mg (1.33 mmol) of allyl (5R,6S)-2-(4-pyridylthio)-6-[(1R)-1-hydroxyethyl]-carbapen-2-em-3-carboxylate in 3.4 ml of anhydrous dichloromethane, and the mixture was stirred at room temperature for 1 h. It was then diluted with 20 ml of anhydrous acetone. The precipitate was filtered off with suction and vigorously stirred with 50 ml of ether for 0.5 h, again filtered off with suction and dried over P4O10 under high vacuum. 361 mg (83%) of the title compound were obtained as a colorless hygroscopic powder.

Workup

  1. filtrationThe precipitate was filtered off with suction
  2. stirringvigorously stirred with 50 ml of ether for 0.5 h
  3. filtrationagain filtered off with suction
  4. dry with materialdried over P4O10 under high vacuum

Sources & evidence

ORD record
ord-016d7c3d05e8424a990cab2d15fc23c3
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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