Sodium Hydroxide → HCID 66788889, compound

HRID 1660799Notes

Reaction equation

HRID 1660799 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10][N:9]2[S:23]([C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[O:33][CH3:34])(=[O:25])=[O:24])=[O:5])C.[OH-].[Na+]>O1CCCC1.CO>[C:19]([O:18][C:16]([N:12]1[C:13]2[C:8](=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:15][CH:14]=2)[N:9]([S:23]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[O:33][CH3:34])(=[O:25])=[O:24])[CH2:10][CH2:11]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66788954HCID 66788954, compound

Product 1

HCID 66788889HCID 66788889, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-quinoxaline-1,6-dicarboxylic acid 1-tert-butyl ester 6-ethyl ester (430 mg, 0.84 mmol) in tetrahydrofuran (10 mL) and methanol (10 mL) was treated with 2N NaOH (5 mL). The mixture was stirred at room temperature for 1 hour. The organic solvents were then partially removed and the residue acidified with HCl 1N (10 mL). The precipitate which formed was filtered, washing with water, and dried under high vacuum. 4-(5-Chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-quinoxaline-1,6-dicarboxylic acid 1-tert-butyl ester was obtained as a light yellow gum, 386 mg (95%), MS (ISP): m/e=481.1 (M−H), which was used crude in the following reaction.

Workup

  1. customThe organic solvents were then partially removed
  2. customThe precipitate which formed
  3. filtrationwas filtered
  4. washwashing with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-309cda6f865741ef9f5c579a5c016083
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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