Acetic Acid → HCID 91000778, compound

HRID 1840438Notes

Reaction equation

HRID 1840438 reaction equation
C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[Si]([O:35][CH2:36][CH2:37][S:38][C:39]1[N:40]=[CH:41][N:42]2[CH:46]=[C:45]([C:47]3[C@H:48]([CH3:71])[C@@H:49]4[C@@H:66]([C@H:67]([OH:69])[CH3:68])[C:65](=[O:70])[N:50]4[C:51]=3[C:52]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=3)=[O:53])[S:44][C:43]=12)(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>C1COCC1.[Cl-].[Na+].O>[OH:69][C@@H:67]([C@H:66]1[C:65](=[O:70])[N:50]2[C:51]([C:52]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=3)=[O:53])=[C:47]([C:45]3[S:44][C:43]4=[C:39]([S:38][CH2:37][CH2:36][OH:35])[N:40]=[CH:41][N:42]4[CH:46]=3)[C@H:48]([CH3:71])[C@H:49]12)[CH3:68]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 11078149TBAF tetrahydrofuranHCID 91321981HCID 91321981, compound

Product 1

HCID 91000778HCID 91000778, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Acetic acid (0.207 ml) and 1.21 ml of a 1 M tetra-n-butylammonium fluoride/THF solution were added to a solution of 265 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-(2-t-butyldimethylsilyloxyethyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 5 ml of THF. The mixture was stirred at room temperature for 6 hr. Brine was added to the reaction solution, and a saturated sodium hydrogencarbonate solution was added thereto. The mixture was adjusted to pH 8.2, and was extracted with ethyl acetate twice. The organic layers were combined, were washed with brine, and were dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to prepare 208 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-[7-(2-hydroxyethyl)thioimidazo[5,1-b]thiazol-2-yl]-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionwas extracted with ethyl acetate twice
  2. washwere washed with brine
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1)
  6. customto prepare 208 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-[7-(2-hydroxyethyl)thioimidazo[5,1-b]thiazol-2-yl]-1-methyl-1-carbapen-2-em-3-carboxylate

Sources & evidence

ORD record
ord-85aec97ca30e426fbd042b87486098ab
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

Loading…