Ethanol → HCID 86592022, compound

HRID 1785891Notes

Reaction equation

HRID 1785891 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[C@@H:15]([CH3:32])[CH2:14]2)[C:9](=[O:12])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].C(O)C>CN(C=O)C>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][CH2:37][CH2:36][O:30][C:27]1[CH:26]=[CH:25][C:24]([C:23]([N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:13]([N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:9](=[O:12])[CH2:10][CH3:11])[CH2:14][C@@H:15]2[CH3:32])=[O:31])=[CH:29][CH:28]=1)[CH3:43]

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 86592023HCID 86592023, compound2×

Product 1

HCID 86592022HCID 86592022, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-Cis-4-(4-{4-[(4-chloro-phenyl)-propionyl-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid ethyl ester was prepared from (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-propionamide. (±)-Cis-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-propionamide (140 mg, 0.31 mmol) was dissolved in DMF (5 mL) at room temperature. Sodium hydride (60% in oil, 32 mg, 0.81 mmol) was added and the mixture allowed to stir 30 min. Ethyl 4-bromobutyrate (207 mg, 1.06 mmol) was added and the reaction was allowed to stir over night. Ethanol was added and the reaction was concentrated in vacuo. The crude residue was purified by silica gel chromatography (80/20 hexanes/ethyl acetate-50/50 hexanes ethyl acetate gradient) to afford the product (171 mg, 0.304 mmol, 98%).

Workup

  1. stirringto stir over night
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe crude residue was purified by silica gel chromatography (80/20 hexanes/ethyl acetate-50/50 hexanes ethyl acetate gradient)

Sources & evidence

ORD record
ord-3480cf13a267421ab349ad761778e341
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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