Dichloromethane → (R)-2-[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-propionimidic acid ethyl ester

HRID 350989Notes

Reaction equation

HRID 350989 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[N:33]=[CH:32][CH:31]=[CH:30][C:12]=3[C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C@@H:24]([C:26](=O)[NH2:27])[CH3:25])=[CH:19][C:18]=3[F:29])=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl[CH2:35]Cl.[CH3:37][OH:38].ClCCl>>[CH2:37]([O:38][C:26](=[NH:27])[C@H:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:13]([C:12]2[C:11]([O:10][C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)=[N:33][CH:32]=[CH:31][CH:30]=2)=[O:14])=[C:18]([F:29])[CH:19]=1)[CH3:25])[CH3:35]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 10275871(R)-2-(benzo[1,3]dioxol-5-yloxy)-N-[4-(1-carbamoyl-ethoxy)-2-fluoro-benzyl]-nicotinamideHCID 21226129Dichloromethane methanol

Product 1

HCID 60128055(R)-2-[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-propionimidic acid ethyl esterYield 38%

Procedure

To a stirred solution of (R)-2-(benzo[1,3]dioxol-5-yloxy)-N-[4-(1-carbamoyl-ethoxy)-2-fluoro-benzyl]-nicotinamide (0.4 g, 0.88 mmol) in dichloromethane (20 ml)triethyloxonium tetrafluoroborate (0.17 g, 0.88 mmol) was added. The reaction was stirred at room temperature 16 h. The reaction was adsorbed onto a small amount of silica gel and column chromatography (2% methanol/dichloromethane) afforded 160 mg of the desired product as a colorless oil (38% yield).

Sources & evidence

ORD record
ord-bee2e3e1960b49a7b9c07d0ee3267aa8
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

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