Potassium Carbonate → HCID 58859753, compound

HRID 1786023Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C@@H:14]([CH3:31])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:38]([O:40][C:41](=[O:46])[CH2:42][CH2:43][CH2:44]Br)[CH3:39]>CN(C=O)C>[CH2:38]([O:40][C:41](=[O:46])[CH2:42][CH2:43][CH2:44][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([N:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:12]([N:8]([C:9](=[O:11])[CH3:10])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:13][C@@H:14]2[CH3:31])=[O:30])=[CH:28][CH:27]=1)[CH3:39]

Participants

Conditions

Temperature: 80 °C

Procedure

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was dissolved in DMF at room temperature and K2CO3 was added. Ethyl-4-bromobutyrate was added and the reaction was allowed to heat to 80° C. overnight. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (50% EtOAc/50% Hexane) to afford the product.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was partitioned between ethyl acetate and water
extractionextracted three times with ethyl acetate
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated down
customThe crude residue was purified by silica gel chromatography (50% EtOAc/50% Hexane)
customto afford the product

Sources & evidence

ORD record: ord-3975f0ddc3c24bc78b568678041c3aa4
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

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