2-Propanesulfonyl chloride → Propane-2-sulfonic acid (5-acetyl-2-benzyloxy-phenyl)-amide

HRID 1061213Notes

Reaction equation

HRID 1061213 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:16](=[O:18])[CH3:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:19]([S:22](Cl)(=[O:24])=[O:23])([CH3:21])[CH3:20]>C(Cl)Cl.N1C=CC=CC=1>[C:16]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([NH:1][S:22]([CH:19]([CH3:21])[CH3:20])(=[O:24])=[O:23])[CH:3]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 155794401-[3-Amino-4-(benzyloxy)phenyl]ethan-1-one

Product 1

HCID 91333667Propane-2-sulfonic acid (5-acetyl-2-benzyloxy-phenyl)-amideYield 30%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-(3-amino-4-benzyloxy-phenyl)-ethanone (EP 0 659 737) (30 g, 125.0 mmol) in CH2Cl2 (500 mL) and pyridine (250 mL) was added dropwise isopropylsufonyl chloride (28.6, 200 mmol) at room temperature. The reaction was stirred for 3 days under nitrogen atmosphere. The mixture was diluted with CH2Cl2 (700 mL) and washed with 1N hydrochloric acid, water, dried over Na2SO4, and concentrated. The product was purified by flash silica gel chromatography eluting with ethyl acetate/hexanes to give the title compound as a white solid(13 g, 30%); 1H NMR (300 MHz, CDCl3) δ 1.35 (d, J=6.9 Hz, 6H), 2.56 (s, 3H), 3.25-3.45 (m, 1H), 5.18 (s, 2H), 6.75 (brs, 1H), 7.02 (d, J=8.6 Hz, 1H), 7.30-7.50 (m, 5H), 7.70 (dd, J=8.6, 2.1 Hz, 1H), 8.18 (d, J=2.1 Hz, 1H); MS (ES) m/z: 364.9 ((M+NH4)+, 100%); HRMS Calcd. for C18H22NO4S(MH+): 348.1264. Found: 348.1259.

Workup

  1. washwashed with 1N hydrochloric acid, water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was purified by flash silica gel chromatography
  5. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-54c03577b8f64c13ab50ecd1c6a993f2
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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