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Potassium Carbonate → 3-(3-Methanesulfonyl-6-methoxy-4-oxo-3,4-dihydro-phthalazin-yl)-propionic acid ethyl ester

HRID 2268919
Notes
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Reaction equation

HRID 2268919 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10](=[O:19])[NH:9][N:8]=1)[CH3:2].[H-].[Na+].[CH3:23][S:24](Cl)(=[O:26])=[O:25].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10](=[O:19])[N:9]([S:24]([CH3:23])(=[O:26])=[O:25])[N:8]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chloride2×HCID 9903689HCID 9903689, compound

Product 1

HCID 698318053-(3-Methanesulfonyl-6-methoxy-4-oxo-3,4-dihydro-phthalazin-yl)-propionic acid ethyl esterYield 17.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of 3-(6-methoxy-4-oxo-3,4-dihydro-phthalazin-1-yl)-propionic acid ethyl ester (4 g, 0.0145 mole), prepared as described in example 119, and NaH (0.638 g, 0.016 mole) in acetonitrile (80 ml) was heated at 55° C. After 2 hours the mixture was cooled, added with methanesulfonyl chloride (1.35 ml, 0.017 mole), and stirred at room temperature overnight. K2CO3 (2 g, 0.0145 mole) and methanesulfonyl chloride (1.12 ml, 0.0145 mole) were added, and the mixture was stirred overnight, then dried and partitioned between water and CHCl3. The organic phase was washed with a K2CO3 solution, anhydrified and dried to give a residue which was chromatographed (eluent: CH2Cl2/ethyl acetate 95:5). The resultant solid was crystallised from acetonitrile (5 ml) to give 0.9 g of the title compound (yield: 17.5%).

Workup

  1. customprepared
  2. temperatureAfter 2 hours the mixture was cooled
  3. stirringthe mixture was stirred overnight
  4. customdried
  5. custompartitioned between water and CHCl3
  6. washThe organic phase was washed with a K2CO3 solution
  7. customdried
  8. customto give a residue which
  9. customwas chromatographed (eluent: CH2Cl2/ethyl acetate 95:5)
  10. customThe resultant solid was crystallised from acetonitrile (5 ml)

Sources & evidence

ORD record
ord-92ee133d373a4bdb8048506c0e64dd14
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06329370B1

Reaction notes

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