Acetic Acid → HCID 131725314, compound

HRID 891499Notes

Reaction equation

HRID 891499 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[N:15]=[C:16]([N:19]2[CH2:22][CH:21]([S:23][C:24]3[C@H:25]([CH3:48])[C@@H:26]4[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:27]4[C:28]=3[C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[CH2:20]2)[S:17][CH:18]=1)=[O:13])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[N:15]=[C:16]([N:19]2[CH2:20][CH:21]([S:23][C:24]3[C@H:25]([CH3:48])[C@@H:26]4[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:27]4[C:28]=3[C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[CH2:22]2)[S:17][CH:18]=1)=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131725313HCID 131725313, compound

Product 1

HCID 131725314HCID 131725314, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of p-nitrobenzyl (1R,5S,6S)-2-(1-{4-[2-(t-butyldimethylsilyloxy)ethylcarbamoyl]-1,3-thiazol-2-yl]azetidin-3-yl)thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (605.3 mg, 0.84 mmol) in tetrahydrofuran (30 ml) were added acetic acid (0.15 ml, 2.6 mmol) and a solution of 1 M tetrabutylammonium fluoride in tetrahydrofuran (2.5 ml, 2.5 mmol) in an ice bath and the mixture was stirred for 1 hour at room temperature. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by: chromatography on a silica gel column using toluene: acetonitrile (2:3) as the eluant to afford p-nitrobenzyl (1R,5S,6S)-2-{1-[4-(2-hydroxyethylcarbamoyl)-1,3-thiazol-2-yl]azetidin-3-yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (383.7 mg, yield 75%) as a pale yellow solid.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by: chromatography on a silica gel column

Sources & evidence

ORD record
ord-c88e47a016694e478b33dcfca4865630
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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