Potassium Carbonate → N-[3-hydroxy-2-(7-methoxy-1-naphthyl)propyl]propionamide

HRID 2374727Notes

Reaction equation

Cl.[NH2:2][CH2:3][CH:4]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].[Cl-].[CH2:26]([OH:29])[CH2:27][CH3:28]>O.C(OCC)(=O)C>[OH:6][CH2:5][CH:4]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:3][NH:2][C:26](=[O:29])[CH2:27][CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

The compound obtained in Step B (3.73 mmol) is dissolved in 100 ml of a mixture of water and ethyl acetate (50/50). Potassium carbonate (11.2 mmol) is added and the reaction mixture is cooled to 0° C. Using an ice bath. Propanol chloride (4.6 mmol) is added dropwise and the mixture is stirred for 15 minutes in the cold state. When the reaction is complete, the organic phase is washed with hydrochloric acid solution (1M), washed with water, dried and evaporated under reduced pressure. The solution obtained is recrystallized from acetonitrile to yield the title product in the form of a white solid.

Workup

washthe organic phase is washed with hydrochloric acid solution (1M)
washwashed with water
customdried
customevaporated under reduced pressure
customThe solution obtained
customis recrystallized from acetonitrile

Sources & evidence

ORD record: ord-8aab6b6d8ade4254a73129bf8d4f58e8
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462741B2

Reaction notes

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