Benzenesulfonyl chloride → 3-{3-[(Benzenesulfonyl-benzo[1,3]dioxol-5-ylmethyl-amino)-methyl]-phenyl}-propionic acid methyl ester

HRID 2300540Notes

Reaction equation

HRID 2300540 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][CH2:14][C:15]2[CH:23]=[CH:22][C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=2)[CH:7]=1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([S:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:33])=[O:32])[CH2:14][C:15]2[CH:23]=[CH:22][C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 540353743-(3-{[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

Product 1

HCID 538030023-{3-[(Benzenesulfonyl-benzo[1,3]dioxol-5-ylmethyl-amino)-methyl]-phenyl}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound of Step B was prepared following the method described in Step A of Example 1 from 3-(3-{[(benzo[1,3]dioxol-5-ylmethyl)-amino]-methyl}-phenyl)-propionic acid methyl ester of Step A and benzenesulfonyl chloride using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 7.85 (d, 2H), 7.62-7.50 (m, 3H), 7.13 (m, 1H), 7.03 (m, 1H), 6.88 (m, 1H), 6.78 (s, 1H), 6.62 (d, 1H), 6.54 (s, 1H), 6.46 (d, 1H), 5.90 (s, 2H), 4.28 (s, 2H), 4.21 (s, 2H), 3.67 (s, 3H), 2.81 (t, 2H), 2.50 (t, 2H).

Sources & evidence

ORD record
ord-10c595ade18c42ddbc468f86cc2e5654
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

Loading…