Water → 4-(3-Pyridylthiomethyl)-2-(2-methylphenyl)benzoic acid methyl ester

HRID 2121240Notes

Reaction equation

HRID 2121240 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Cl)=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].[K].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([SH:27])[CH:22]=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:27][C:23]2[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=2)=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 206999064-Chloromethyl-2-(2-methylphenyl)benzoic acid methyl esterHCID 69893940HCID 69893940, compound

Product 1

HCID 543012374-(3-Pyridylthiomethyl)-2-(2-methylphenyl)benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution in DMF (2 mL) of 4-chloromethyl-2-(2-methylphenyl)benzoic acid methyl ester (275 mg, 1.0 mmol) was added 3-pyridinethiol potassium salt (224 mg, 1.5 mmol). The reaction mixture was stirred for 30 minutes and then was poured into water. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with water and brine, dried, filtered and concentrated in vacuo. Chromatography on silica gel (40% ethyl acetate-hexanes) gave 4-(3-pyridylthiomethyl)-2-(2-methylphenyl)benzoic acid methyl ester which was converted to the title compound by saponification of the methyl ester, coupling with methionine methyl ester hydrochloride, and saponification as described in Examples 319I-J. 1H NMR (300 MHz, DMSO-d6) δ 12.53 (bs, 1H), 8.49 (d, 1H), 8.38 (dd, 1H), 8.11 (d, 1H), 7.79 (dt, 1H), 7.43 (s, 2H), 7.31 (dd, 1H), 7.19 (m, 2H), 7.11 (m, 2H), 7.05 (m, 1H), 4.36 (s, 2H), 4.20 (m, 1H), 1.92-2.23 (m, 8H), 1.66-1.90 (m, 2H). MS (CI, NH3) m/e 467, 449. Anal calcd for C25H26N2O3S2: C, 64.35; H, 5.62; N, 6.00. Found: C, 64.00; H, 5.62; N, 5.89.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7222cc0fa67941758a2dc3e2e2146a5a
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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