Hydrochloric Acid → HCID 11304295, compound

HRID 565088Notes

Reaction equation

HRID 565088 reaction equation
[CH2:1]([N:8]([C@@H:16]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:17](=[O:22])[CH2:18][S:19]([CH3:21])=O)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])[OH:32].[Na+]>CS(C)=O>[CH2:1]([N:8]([C@@H:16]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:17](=[O:22])[CH:18]([OH:32])[S:19][CH3:21])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11235137HCID 11235137, compound

Product 1

HCID 11304295HCID 11304295, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

309.6 mg (0.763 mmol) of (3S)-3-(N,N-dibenzyl)amino-1-methylsulfinyl-2-oxo-4-phenylbutane was dissolved in 6 ml of dimethylsulfoxide, and 1.5 ml of 2 N hydrochloric acid was added thereto and stirred at room temperature for 16 hours. While being cooled in an ice bath, this was neutralized with 5 ml of a saturated aqueous solution of sodium hydrogen carbonate, and then subjected to phase separation with 20 ml of ethyl acetate and 10 ml of water. The resulting aqueous layer was extracted twice with 10 ml of ethyl acetate. The organic layers were combined, then washed with 20 ml of water and 20 ml of a saturated saline solution in that order, and thereafter dried with anhydrous sodium sulfate. This was filtered and concentrated to obtain 371.5 mg of a crude product of the above-entitled compound.

Workup

  1. temperatureWhile being cooled in an ice bath
  2. customsubjected to phase separation with 20 ml of ethyl acetate and 10 ml of water
  3. extractionThe resulting aqueous layer was extracted twice with 10 ml of ethyl acetate
  4. washwashed with 20 ml of water and 20 ml of a saturated saline solution in that order
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationThis was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4a5181e510ea4d3fbb8f0d6ef7f46bd6
Source dataset
uspto-grants-2001_01
Patent number
US06169200A

Reaction notes

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