Acetic Acid → HCID 131722319, compound

HRID 568232Notes

Reaction equation

HRID 568232 reaction equation
C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[CH2:28]([O:31][C:32]([N:34]1[C@H:38]([CH:39]([OH:48])[C:40]2[N:41]=[CH:42][N:43]3[CH:47]=[CH:46][S:45][C:44]=23)[CH2:37][C@H:36]([S:49][C:50]2[C@H:51]([CH3:74])[C@@H:52]3[C@@H:62]([C@H:63]([O:65][Si](C(C)(C)C)(C)C)[CH3:64])[C:61](=[O:73])[N:53]3[C:54]=2[C:55]([O:57][CH2:58][CH:59]=[CH2:60])=[O:56])[CH2:35]1)=[O:33])[CH:29]=[CH2:30]>C1COCC1.C(OCC)(=O)C>[CH2:28]([O:31][C:32]([N:34]1[C@H:38]([CH:39]([OH:48])[C:40]2[N:41]=[CH:42][N:43]3[CH:47]=[CH:46][S:45][C:44]=23)[CH2:37][C@H:36]([S:49][C:50]2[C@H:51]([CH3:74])[C@@H:52]3[C@@H:62]([C@H:63]([OH:65])[CH3:64])[C:61](=[O:73])[N:53]3[C:54]=2[C:55]([O:57][CH2:58][CH:59]=[CH2:60])=[O:56])[CH2:35]1)=[O:33])[CH:29]=[CH2:30]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11078149TBAF tetrahydrofuranHCID 131722318allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-7-yl)methyl]pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 131722319HCID 131722319, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.60 ml) and 3.5 ml of a 1 M tetra-n-butylammonium fluoride/THF solution are added to a solution of 491 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-7-yl)methyl]pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate (a diastereomer mixture) in 10.5 ml of anhydrous THF, and the mixture is stirred in an argon atmosphere at room temperature for 16 hr. The reaction solution is diluted with 100 ml of ethyl acetate, and the diluted solution is successively washed with a 5% aqueous sodium hydrogencarbonate solution and saturated saline and dried over anhydrous magnesium sulfate, followed by filtration and the removal of the solvent by evaporation to give a dark yellow oil. This oil is purified by column chromatography on silica gel (ethyl acetate:methanol=95:5) to give 353 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-7-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (a diastereomer mixture) as a light yellow amorphous material.

Workup

  1. washthe diluted solution is successively washed with a 5% aqueous sodium hydrogencarbonate solution and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfollowed by filtration
  4. customthe removal of the solvent
  5. customby evaporation
  6. customto give a dark yellow oil
  7. customThis oil is purified by column chromatography on silica gel (ethyl acetate:methanol=95:5)

Sources & evidence

ORD record
ord-e970102387254b8b8a9db76d5e0f91fd
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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