Acetic Acid → HCID 131722313, compound

HRID 568228Notes

Reaction equation

HRID 568228 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:47]3[C:43]([S:44][CH:45]=[CH:46]3)=[CH:42][N:41]=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:47]3[C:43]([S:44][CH:45]=[CH:46]3)=[CH:42][N:41]=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 131722314HCID 131722314, compound

Product 1

HCID 131722313HCID 131722313, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.19 ml) and 1.1 ml of a 1 M tetra-n-butylammonium fluoride/THF are added to a solution of 155 mg of the high polar component (stereoisomer A) of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-5-yl)methyl]pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate in 3.3 ml of anhydrous THF, and the mixture is stirred in an argon atmosphere at room temperature for 39 hr. The reaction solution is diluted with 30 ml of ethyl acetate, and the diluted solution is washed with semi-saturated saline and dried over anhydrous magnesium sulfate, followed by filtration and the removal of the solvent by evaporation to give a slightly yellow oil. This oil is successively purified by column chromatography on silica gel (ethyl acetate:methanol=95:5) and on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 117 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-5-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (stereoisomer A) as a yellow viscous material.

Workup

  1. washthe diluted solution is washed with semi-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 slightly yellow oil
  7. customThis oil is successively purified by column chromatography on silica gel (ethyl acetate:methanol=95:5) and on Sephadex

Sources & evidence

ORD record
ord-d4be6617483d4bc3a07d9fa85f8f2841
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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