Anisole → HCID 10253779, compound

HRID 2254600Notes

Reaction equation

HRID 2254600 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([Cl:31])[N:24]=[C:23]2[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([Cl:31])[N:24]=[C:23]2[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:19][CH:20]=1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 86745954HCID 86745954, compound

Product 1

HCID 10253779HCID 10253779, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-((2'-((tert-butylamino)sulfonyl)(1,1'-biphenyl)-4yl)methyl)-2-butyl-4-chloro-imidazole-5-carboxylic acid, methyl ester (75.0 mg, 0.145 mmol) was stirred in trifluoroacetic acid (1.0 ml) containing anisole (20 μl) under nitrogen at room temperature for 24 hours. The trifluoroacetic acid was removed in vacuo and the residue chromatographed (silica gel, 35% ethyl acetate-hexane) to afford 1-((2'-(aminosulfonyl)(1,1'-biphenyl)-4-yl)methyl)-2-butyl-4-chloro-imidazole-5-carboxylic acid, methyl ester (67.5 mg, 100%) as a white solid; 1H NMR (300 MHz, CD3OD/CDCl3) δ8.08 (d, J=7.7 Hz, 1H), 7.54 (t, J=7.7 Hz, 1H), 7.46 (t, J=7.7 Hz, 1H), 7.40 (d, J=8.1 Hz, 2H), 7.26 (d, J=7.7 Hz, 1H), 7.04 (d, J=8.1 Hz, 2H), 5.57 (s, 2H), 3.80 (s, 3H), 2.64 (t, J=7.4 Hz, 2H), 1.62 (quin, J=7.4 Hz, 2H), 1.31 (sext, J=7.4 Hz, 2H), 0.89 (t, J=7.4 Hz, 3H).

Workup

  1. customThe trifluoroacetic acid was removed in vacuo
  2. customthe residue chromatographed (silica gel, 35% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-37401d460a2a4843b9ff75c51c423dbf
Source dataset
uspto-grants-1993_08
Patent number
US05236928

Reaction notes

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