2-Thiazolesulfonyl chloride → 3-(3-{[(4-tert-Butyl-benzyl)-(thiazole-2-sulfonyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2300544Notes

Reaction equation

HRID 2300544 reaction equation
[CH3:1][O:2][C:3](=[O:25])[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:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH:7]=1.[S:26]1[CH:30]=[CH:29][N:28]=[C:27]1[S:31](Cl)(=[O:33])=[O:32]>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:25])[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]([C:21]([CH3:22])([CH3:24])[CH3:23])=[CH:19][CH:20]=2)[S:31]([C:27]2[S:26][CH:30]=[CH:29][N:28]=2)(=[O:33])=[O:32])[CH:7]=1

Participants

4

Reactant 2

HCID 115792352-Thiazolesulfonyl chlorideHCID 543643433-{3-[(4-tert-Butyl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Product 1

HCID 541915713-(3-{[(4-tert-Butyl-benzyl)-(thiazole-2-sulfonyl)-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-[(4-tert-butyl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester, prepared in Step A of Example 12s, and thiazole-2-sulfonyl chloride using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 7.93 (d, 1H), 7.56 (d, 1H), 7.23 (d, 2H), 7.14 (m, 1H), 7.04 (m, 3H), 6.98 (m, 2H), 4.47 (s, 2H), 4.41 (s, 2H), 3.67 (s, 3H), 2.84 (t, 2H), 2.54 (t, 2H), 1.27 (s, 9H); MS 487 (M+1).

Sources & evidence

ORD record
ord-71821327583541538c918bb94e0d88cc
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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