Acetic Acid → HCID 131722293, compound

HRID 568216Notes

Reaction equation

HRID 568216 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]([C:39]([N:41]([CH2:43][C:44]2[N:51]3[C:47]([S:48][CH:49]=[CH:50]3)=[CH:46][N:45]=2)[CH3:42])=[O:40])[CH2:37][C@H:36]([S:52][C:53]2[C@H:54]([CH3:77])[C@@H:55]3[C@@H:65]([C@H:66]([O:68][Si](C(C)(C)C)(C)C)[CH3:67])[C:64](=[O:76])[N:56]3[C:57]=2[C:58]([O:60][CH2:61][CH:62]=[CH2:63])=[O:59])[CH2:35]1)=[O:33])[CH:29]=[CH2:30].P([O-])([O-])([O-])=O>C1COCC1>[CH2:28]([O:31][C:32]([N:34]1[C@H:38]([C:39]([N:41]([CH2:43][C:44]2[N:51]3[C:47]([S:48][CH:49]=[CH:50]3)=[CH:46][N:45]=2)[CH3:42])=[O:40])[CH2:37][C@H:36]([S:52][C:53]2[C@H:54]([CH3:77])[C@@H:55]3[C@@H:65]([C@H:66]([OH:68])[CH3:67])[C:64](=[O:76])[N:56]3[C:57]=2[C:58]([O:60][CH2:61][CH:62]=[CH2:63])=[O:59])[CH2:35]1)=[O:33])[CH:29]=[CH2:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1061PhosphateHCID 11078149TBAF tetrahydrofuranHCID 131722294HCID 131722294, compound

Product 1

HCID 131722293HCID 131722293, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (0.132 ml) and 0.77 ml of a 1 M tetra-n-butylammonium fluoride/THF solution are added to a solution of 114 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[N-(imidazo[5,1-b]thiazol-5-yl)methyl-N-methylaminocarbonyl]pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl)-1-methyl-carbapen-2-em-3-carboxylate in 2.3 ml of anhydrous THF, and the mixture is stirred in an argon atmosphere at room temperature for 22.5 hr. 1/15 M phosphate buffer (pH 7.0) (3 ml) is added thereto, and the mixture is extracted twice with 15 ml of ethyl acetate. The combined organic layers are dried over anhydrous magnesium sulfate and filtered, and the solvent is removed under reduced pressure and by filtrate to give a yellowish orange oil. This oil is purified by column chromatography on silica gel (ethyl acetate:methanol=9:1) to give 78.3 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[N-(imidazo[5,1-b]thiazol-5-yl)methyl-N-methylaminocarbonyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate as a colorless solid.

Workup

  1. extractionthe mixture is extracted twice with 15 ml of ethyl acetate
  2. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent is removed under reduced pressure and by filtrate
  5. customto give a yellowish orange oil
  6. customThis oil is purified by column chromatography on silica gel (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-4484cacdf5f2438daaa9290941aee318
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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