Hydrochloric Acid → HCID 53639037, compound

HRID 2298171Notes

Reaction equation

HRID 2298171 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[CH2:7]([O:9][C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[CH:13]=1)[CH3:8].C(N(CC)CC)C.Cl>C(Cl)Cl>[CH2:7]([O:9][C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH:13]=1)[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69544396Ethyl [3-(aminomethyl)phenyl]acetate--hydrogen chloride (1/1)

Product 1

HCID 53639037HCID 53639037, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (2.6 mL, 34 mmol) was slowly added to a solution of (3-aminomethyl-phenyl)-acetic Acid ethyl ester hydrochloride (7.31 g, 34 mmol) and triethylamine (9.8 mL, 70 mmol) in CH2Cl2 (100 mL) at 0° C. The mixture was stirred for 1 h and 1N aqueous HCl solution was added. The aqueous solution was extracted with CH2Cl2 (3×) and the combined organic extracts were washed with brine. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (1:1 hexanes:EtOAc) provided the title sulfonamide (8.56 g) as a clear and colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.34-7.21 (m, 4H), 4.70 (broad, 1H), 4.29 (d, 2H), 4.12 (q, 2H), 3.60 (s, 2H), 2.86 (s, 3H), 1.24 (t, 3H).

Workup

  1. extractionThe aqueous solution was extracted with CH2Cl2 (3×)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-ee00c523e01e4fdaa09829c741d4decf
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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