Hydrochloric Acid → HCID 9844305, compound

HRID 1374385Notes

Reaction equation

HRID 1374385 reaction equation
C(OC([N:7]1[C@H:11]([CH3:12])[CH:10]=[C:9]([C:13]2[N:14]=[C:15]([S:18][C:19]3[C@H:25]([CH3:26])[C@H:24]4[N:21]([C:22](=[O:34])[C@@H:23]4[C@H:27]([O:29][Si](C)(C)C)[CH3:28])[C:20]=3[C:35]([O:37]CC=C)=[O:36])[S:16][CH:17]=2)[CH2:8]1)=O)C=C.O.Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C1COCC1>[OH:29][C@@H:27]([C@H:23]1[C:22](=[O:34])[N:21]2[C@@H:24]1[C@@H:25]([CH3:26])[C:19]([S:18][C:15]1[S:16][CH:17]=[C:13]([C:9]3[CH2:8][NH:7][C@H:11]([CH3:12])[CH:10]=3)[N:14]=1)=[C:20]2[C:35]([OH:37])=[O:36])[CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 86592501HCID 86592501, compound

Product 1

HCID 9844305HCID 9844305, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(4-{(5R)-1-[(allyloxy)carbonyl]-5-methyl-2,5-dihydro-1H-pyrrol-3-yl}-1,3-thiazol-2-yl)sulfanyl]-4-methyl-7-oxo-6-[(1R)-1-[(trimethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (42 mg, 0.070 mmol) in ethyl acetate (4 ml) was added water and then 2N hydrochloric acid and the solution was adjusted to pH 2. After stirring for 10 minutes, THF was further added thereto and the solution was stirred for 20 minutes. To the obtained mixture was added a saturated aqueous sodium hydrogen carbonate solution and the solution was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To a solution of the residue (37.6 mg) in dichloromethane (2 ml) were added at 0° C. tributyltin hydride (0.17 ml), acetic acid (10 μl) and bis(triphenylphosphine)palladium chloride(5 mg) and the mixture was stirred at the same temperature for 10 minutes. To the reaction mixture were added phosphate buffer (50 mM, pH7, 25 ml) and dichloromethane (20 ml). The aqueous layer was separated and the dichloromethane layer was extracted twice with water. The combined aqueous layer was washed with dichloromethane (3 ml). The organic solvent in the aqueous layer was evaporated under reduced pressure, and the residue was purified by polymer chromatography (CHP-20P). The fractions eluted with 1–3% aqueous THF solution were combined and lyophilized to give (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-({4-[(5R)-5-methyl-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.

Workup

  1. stirringthe solution was stirred for 20 minutes
  2. extractionthe solution was extracted twice with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. additionTo a solution of the residue (37.6 mg) in dichloromethane (2 ml) were added at 0° C. tributyltin hydride (0.17 ml), acetic acid (10 μl) and bis(triphenylphosphine)palladium chloride(5 mg)
  7. stirringthe mixture was stirred at the same temperature for 10 minutes
  8. additionTo the reaction mixture were added phosphate buffer (50 mM, pH7, 25 ml) and dichloromethane (20 ml)
  9. customThe aqueous layer was separated
  10. extractionthe dichloromethane layer was extracted twice with water
  11. washThe combined aqueous layer was washed with dichloromethane (3 ml)
  12. customThe organic solvent in the aqueous layer was evaporated under reduced pressure
  13. customthe residue was purified by polymer chromatography (CHP-20P)
  14. washThe fractions eluted with 1–3% aqueous THF solution

Sources & evidence

ORD record
ord-8d29e0476fc645129205e07d16e328cd
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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