Hydrochloric Acid → HCID 91038447, compound

HRID 1840468Notes

Reaction equation

HRID 1840468 reaction equation
[N:1]([CH2:4][C@@H:5]([O:41][Si](CC)(CC)CC)[CH2:6][S:7][C:8]1[N:9]=[CH:10][N:11]2[CH:15]=[C:14]([C:16]3[C@H:17]([CH3:40])[C@@H:18]4[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]4[C:20]=3[C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[S:13][C:12]=12)=[N+:2]=[N-:3].Cl.C(=O)([O-])O.[Na+]>C1COCC1.O>[N:1]([CH2:4][C@@H:5]([OH:41])[CH2:6][S:7][C:8]1[N:9]=[CH:10][N:11]2[CH:15]=[C:14]([C:16]3[C@H:17]([CH3:40])[C@@H:18]4[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]4[C:20]=3[C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[S:13][C:12]=12)=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 91074096HCID 91074096, compound

Product 1

HCID 91038447HCID 91038447, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-[7-((2R)-3-azido-2-triethylsilyloxypropyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (560 mg) was dissolved in 10 ml of THF and 10 ml of water. The solution was adjusted to pH 2.5 by the addition of 1 N hydrochloric acid. The mixture was stirred at room temperature for 30 min, and was then adjusted to pH 7.0 by the addition of an aqueous sodium hydrogencarbonate solution, followed by extraction 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 455 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-((2R)-3-azido-2-hydroxypropyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionfollowed by extraction 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 455 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-((2R)-3-azido-2-hydroxypropyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Sources & evidence

ORD record
ord-99b0b7a90abf484eb01786e27968c593
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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