1-(2-Bromoethoxy)-3-chlorobenzene → 3-[3-({Benzenesulfonyl-[2-(3-chloro-phenoxy)-ethyl]-amino}-methyl)-phenyl]-propionic acid methyl ester

HRID 2300549Notes

Reaction equation

HRID 2300549 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:7]=1.Br[CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1>>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 25077201-(2-Bromoethoxy)-3-chlorobenzeneHCID 539708643-[3-(Benzenesulfonylamino-methyl)-phenyl]-propionic acid methyl ester

Product 1

HCID 540725013-[3-({Benzenesulfonyl-[2-(3-chloro-phenoxy)-ethyl]-amino}-methyl)-phenyl]-propionic acid methyl ester

Procedure

Following the procedure described in Step A of Example 2, 3-[3-(benzenesulfonylamino-methyl)-phenyl]-propionic acid methyl ester was alkylated with 1-(2-bromo-ethoxy)-3-chloro-benzene to provide the title compound of Step A. 1H NMR (400 MHz, CDCl3) δ 7.86 (dd, 2H), 7.60-7.49 (m, 3H), 7.22 (d, 1H), 7.13-7.06 (m, 4H), 6.88 (m, 1H), 6.60 (d, 1H), 6.52 (m, 1H), 4.42 (s, 2H), 3.88 (s, 2H), 3.65 (s, 3H), 3.47 (t, 2H), 2.87 (t, 2H), 2.54 (t, 2H).

Sources & evidence

ORD record
ord-44df61e9ebe8455db61ec0474632b6d2
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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