4-Fluorobenzenesulfonyl chloride → 3-(3-{[(2,3-Dihydro-benzofuran-5-ylmethyl)-(4-fluoro-benzenesulfonyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2117541Notes

Reaction equation

HRID 2117541 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:16]=[CH:17][C:18]3[O:22][CH2:21][CH2:20][C:19]=3[CH:23]=2)[CH:7]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=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]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]3[O:22][CH2:21][CH2:20][C:19]=3[CH:23]=2)[S:32]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[CH:7]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 541084383-(3-{[(2,3-Dihydro-benzofuran-5-ylmethyl)-amino]methyl}-phenyl)-propionic acid methyl ester

Product 1

HCID 537506433-(3-{[(2,3-Dihydro-benzofuran-5-ylmethyl)-(4-fluoro-benzenesulfonyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound of Step A was prepared following the method described in Step A of Example 1 from 3-(3-{[(2,3-dihydro-benzofuran-5-ylmethyl)-amino]methyl}-phenyl)-propionic acid methyl ester, prepared in Step A of Example 12w, and 4-fluorobenzenesulfonyl chloride using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ7.79 (m, 2H), 7.14 (m, 3H), 7.03 (d, 1H), 6.88 (m, 2H), 6.79 (s, 1H), 6.71 (d, 1H), 6.58 (d, 1H), 4.51 (t, 2H), 4.25 (s, 2H), 4.21 (s, 2H), 3.64 (s, 3H), 3.08 (t, 2H), 2.80 (t, 2H), 2.50 (t, 2H).

Sources & evidence

ORD record
ord-65a270c45dc544ed97c63d7f7d5f3226
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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