Hydrochloric Acid → HCID 69571538, compound

HRID 1071976Notes

Reaction equation

HRID 1071976 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14](=[O:22])[C@H:13]2[CH2:23][C:24](OC)=[O:25])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14](=[O:22])[C@H:13]2[CH2:23][CH2:24][OH:25])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11212538HCID 11212538, compound

Product 1

HCID 69571538HCID 69571538, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl {(2R)-1-[(3,4-dichlorophenyl)sulfonyl]-3oxo-1,2,3,4-tetrahydroquinoxalin-2-yl}acetate (Example 1, Step 3, 371 mg, 0.86 mmol) in THF (2 mL) was added LiAlH(tBuO)3 (3 mL, 3 mmol). The reaction mixture was stirred at room temperature for approximately two weeks and was then poured into 1N HCl (30 mL) and extracted with EtOAc (3×20 mL). The combined organics were washed with brine (1×20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was subjected to silica gel chromatography eluting with 2%-7% MeOH in CH2Cl2 to give (3R)-4-[(3,4-dichlorophenyl)sulfonyl]-3-(2-hydroxyethyl)-3,4-dihydroquinoxalin-2(1H)-one (211 mg, 61%). LCMS (ES) 400.8.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organics were washed with brine (1×20 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washeluting with 2%-7% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f840dccf1a5d45e5a9f31705b174bfcc
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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