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

HRID 2268919Notes

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]

Participants

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

customprepared
temperatureAfter 2 hours the mixture was cooled
stirringthe mixture was stirred overnight
customdried
custompartitioned between water and CHCl3
washThe organic phase was washed with a K2CO3 solution
customdried
customto give a residue which
customwas chromatographed (eluent: CH2Cl2/ethyl acetate 95:5)
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

Loading…