Hydrochloric Acid → HCID 15338475, compound

HRID 2305370Notes

Reaction equation

[NH2:1][CH:2]([CH:6]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)[C:3]([OH:5])=[O:4].[CH3:23][O:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[N:28]=[C:27](S(C)(=O)=O)[N:26]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(OCC)(=O)C.O.CN(C=O)C>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=2)[CH:2]([NH:1][C:27]2[N:28]=[C:29]([O:31][CH3:32])[CH:30]=[C:25]([O:24][CH3:23])[N:26]=2)[C:3]([OH:5])=[O:4])[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2.20 g (7.3 mmol) of 2-amino-3,3-di(3-methoxyphenyl)propionic acid, 0.66 g (3.04 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.39 g (3.65 mmol) of sodium carbonate were introduced into a mixture of 16 ml of DMF and 16 ml of water and stirred at 80° C. for 10 hours. Water and ethyl acetate were then added to the reaction mixture. The aqueous phase was acidified with 6 normal hydrochloric acid and extracted three times with ethyl acetate. Drying with MgSO4 and concentration resulted in the crude product, which was chromatographed on silica gel with dichloromethane/methanol (50:1). 0.455 g (34.1%) of a white powder of melting point 58-66° C. was obtained.

Workup

extractionextracted three times with ethyl acetate
dry with materialDrying with MgSO4 and concentration
customresulted in the crude product, which
customwas chromatographed on silica gel with dichloromethane/methanol (50:1)

Sources & evidence

ORD record: ord-2889e9e171d7475393f217a17d1a0a33
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06440975B1

Reaction notes

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