Hydrochloric Acid → (3-{[Methanesulfonyl-(4-methyl-benzyl)amino]-methyl}-phenyl)-acetic acid ethyl ester

HRID 890778Notes

Reaction equation

HRID 890778 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[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]([CH3:21])=[CH:17][CH:16]=2)[CH:7]=1)[CH3:2].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].Cl>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([S:31]([CH3:30])(=[O:33])=[O:32])[CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53797538(3-{[(4-Methyl-benzyl)-amino]-methyl}-phenyl)-acetic Acid Ethyl Ester

Product 1

HCID 53833369(3-{[Methanesulfonyl-(4-methyl-benzyl)amino]-methyl}-phenyl)-acetic acid ethyl esterYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-{[(4-methyl-benzyl)-amino]-methyl}-phenyl)-acetic acid ethyl ester (119 mg, 0.401 mmol) and triethylamine (0.61 mL, 0.726 mmol) in CH2Cl2 (2 mL) at 0° C. was added methanesulfonyl chloride (0.031 mL, 0.405 mmol). The reaction was stirred at room temperature for 2.5 h and 1N HCl was added. The product was extracted into CH2Cl2 (3×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by medium pressure chromatography (3:1 hexanes:EtOAc) to provide the title compound (101.4 mg). 1H NMR (400 MHz, CDCl3) δ 7.13–7.36 (m, 8H), 4.27–4.30 (m, 4H), 4.14 (q, 2H), 3.60 (s, 2H), 2.74 (s, 3H), 2.33 (s, 3H); MS 376 (M+1).

Workup

  1. extractionThe product was extracted into CH2Cl2 (3×)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by medium pressure chromatography (3:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-18a5a579f79a4460a5b6978f6533ccfb
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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