Hydrochloric Acid → HCID 86607073, compound

HRID 2376666Notes

Reaction equation

HRID 2376666 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[C:11]([CH2:12][NH:13][C:14](=[O:44])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH2:28][C@H:27]4[N:24]([C:25](=[O:36])[C@@H:26]4[C@H:29]([O:31][Si](C)(C)C)[CH3:30])[C:23]=3[C:37]([O:39][CH2:40][CH:41]=[CH2:42])=[O:38])=[CH:18][C:17]=2[Cl:43])=[CH:10][N:9]=[CH:8]1)=[O:6])[CH:2]=[CH2:3].Cl.C(=O)(O)[O-]>C1COCC1.O.[Cl-].[Na+].O>[CH2:1]([O:4][C:5]([N:7]1[C:11]([CH2:12][NH:13][C:14](=[O:44])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH2:28][C@H:27]4[N:24]([C:25](=[O:36])[C@@H:26]4[C@H:29]([OH:31])[CH3:30])[C:23]=3[C:37]([O:39][CH2:40][CH:41]=[CH2:42])=[O:38])=[CH:18][C:17]=2[Cl:43])=[CH:10][N:9]=[CH:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 86607074HCID 86607074, compound

Product 1

HCID 86607073HCID 86607073, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Allyl (5R,6S)-3-(4-{2-[({1-[(allyloxy)carbonyl]-1H-imidazol-5-yl}methyl)amino]-2-oxoethyl}-3-chlorophenyl)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.78 g, 1.22 mmol) prepared by step c) was dissolved in THF (23 ml) and water (11 ml), and the solution was cooled in a water bath. Thereto was gradually dropped using a pH meter, 0.1N hydrochloric acid to adjust pH to 3.0. Fifteen minutes later, pH of the solution was adjusted 6.8 by gradually dropping saturated bicarbonate solution thereto, and then saturated brine (50 ml) was added. The solution was extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated to give allyl (5R,6S)-3-(4-{2-[({1-[(allyloxy)carbonyl]-1H-imidazol-5-yl}methyl)amino]-2-oxoethyl}-3-chlorophenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.54 g, yield 78%) as a pale yellow amorphous.

Workup

  1. additionThereto was gradually dropped
  2. customFifteen minutes
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f408ac9958d44c9943cf66b37c9f239
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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