Hydrochloric Acid → HCID 86592503, compound

HRID 1374387Notes

Reaction equation

HRID 1374387 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[C@@H:12]([CH3:13])[CH:11]=[C:10]([C:14]2[N:15]=[C:16]([S:19][C:20]3[C@H:26]([CH3:27])[C@H:25]4[N:22]([C:23](=[O:35])[C@@H:24]4[C@H:28]([O:30][Si](C)(C)C)[CH3:29])[C:21]=3[C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])[S:17][CH:18]=2)[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3].O.Cl.C(=O)([O-])O.[Na+]>C1COCC1>[CH2:1]([O:4][C:5]([N:7]1[C@@H:12]([CH3:13])[CH:11]=[C:10]([C:14]2[N:15]=[C:16]([S:19][C:20]3[C@H:26]([CH3:27])[C@H:25]4[N:22]([C:23](=[O:35])[C@@H:24]4[C@H:28]([OH:30])[CH3:29])[C:21]=3[C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])[S:17][CH:18]=2)[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 10875843HCID 10875843, compound

Product 1

HCID 86592503HCID 86592503, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(4-{(6S)-1-[(allyloxy)carbonyl]-6-methyl-1,2,3,6-tetrahydro-4-pyridinyl}-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 (640 mg, 1.04 mmol) in THF (30 ml) was added at 0° C. water and then the solution was adjusted to pH about 3 with 1N hydrochloric acid and stirred for 10 minutes. To the reaction solution was added an aqueous sodium hydrogen carbonate solution and the reaction mixture was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the solvent in vacuo, the residue was purified with silica gel chromatography (hexane/ethyl acetate=1/2) to give allyl (4R,5S,6S)-3-[(4-{(6S)-1-[(allyloxy)carbonyl]-6-methyl-1,2,3,6-tetrahydro-4-pyridinyl}-1,3-thiazol-2-yl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (547 mg, 97%) as a pale yellowish amorphous.

Workup

  1. extractionthe reaction mixture was extracted twice with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of the solvent in vacuo
  5. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-11eecc99698d41569958208d05dffdc2
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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