Acetic Acid → HCID 131722300, compound

HRID 568221Notes

Reaction equation

HRID 568221 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]3[CH:47]=[N:46][CH:45]=[C:42]3[S:43][CH:44]=2)[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]3[CH:47]=[N:46][CH:45]=[C:42]3[S:43][CH:44]=2)[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 131722303allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 131722300HCID 131722300, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.26 ml) and 1.52 ml of a 1 M tetra-n-butyl ammonium fluoride/THF solution are added to a solution of 213 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate (stereoisomer B) in 4.5 ml of anhydrous THF, and the mixture is stirred in an argon atmosphere at room temperature for 38 hr. The reaction solution is diluted with 80 ml of ethyl acetate, the diluted solution is successively washed with 40 ml of a 1/15 M phosphate buffer (pH 7.0) and 20 ml of saturated saline, the washed solution is dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation to give 193 mg of a slightly yellow oil. This oil is successively purified by column chromatography on silica gel (ethyl acetate:methanol=95:5→9:1) and on Sephadex LH-20 (chloroform:methanol=1:1) to give 119.2 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (stereoisomer B) as a milky white amorphous material.

Workup

  1. washthe diluted solution is successively washed with 40 ml of a 1/15 M phosphate buffer (pH 7.0) and 20 ml of saturated saline
  2. dry with materialthe washed solution is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent is removed by evaporation
  5. customto give 193 mg of a slightly yellow oil
  6. customThis oil is successively purified by column chromatography on silica gel (ethyl acetate:methanol=95:5→9:1) and on Sephadex

Sources & evidence

ORD record
ord-0ad80350bb3f42488ec006f7b06ea45c
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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