Sulfuryl chloride → (3-{[(5-Chloro-thiophene-2-sulfonyl)-(4-thiazol-2-yl-benzyl)-amino]-methyl}-phenoxy)-acetic acid tert-butyl ester

HRID 2117576Notes

Reaction equation

HRID 2117576 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[CH:20][CH:19]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:30][C:31]1[S:35][C:34]([S:36](Cl)(=[O:38])=[O:37])=[CH:33][CH:32]=1.S(Cl)(Cl)(=O)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([S:36]([C:34]2[S:35][C:31]([Cl:30])=[CH:32][CH:33]=2)(=[O:38])=[O:37])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[CH:22][CH:23]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 53752425{3-[(4-Thiazol-2-yl-benzylamino)-methyl]-phenoxy}-acetic Acid Tert-butyl Ester

Product 1

HCID 53997529(3-{[(5-Chloro-thiophene-2-sulfonyl)-(4-thiazol-2-yl-benzyl)-amino]-methyl}-phenoxy)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound of Step A was prepared following the method described in Step A of Example 13w from {3-[(4-thiazol-2-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester, prepared in Step A of Example 13i, and 5-chlorothiophene-2-sulfonyl chloride with the following exception. The sulfonyl chloride was dissolved in CH2Cl2 (1 mL) and 0.28 mL was added to the reaction mixture. 1H NMR (400 MHz, CDCl3) δ 8.03 (d, 1H), 7.79 (d, 2H), 7.43 (d, 1H), 7.34 (d, 1H), 7.24 (m, 3H), 7.13 (m, 1H), 6.94 (d, 1H), 6.76 (m, 1H), 6.68 (m, 2H), 4.41 (s, 2H), 4.35 (s, 2H), 4.30 (s, 2H), 1.48 (s, 9H); MS 591 (M+).

Workup

  1. addition0.28 mL was added to the reaction mixture

Sources & evidence

ORD record
ord-944a4b4559ab465f8ae4decf05e50e25
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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