1-Propanesulfonyl chloride → {3-[(Propane-1-sulfonylamino)-methyl]-phenyl}-acetic acid methyl ester

HRID 842747Notes

Reaction equation

HRID 842747 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH2:13])[CH:7]=1.[CH2:15]([S:18](Cl)(=[O:20])=[O:19])[CH2:16][CH3:17].C(N(CC)C(C)C)(C)C>ClC(Cl)C>[CH3:2][O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][S:18]([CH2:15][CH2:16][CH3:17])(=[O:20])=[O:19])[CH:7]=1

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21185371Methyl 2-[3-(aminomethyl)phenyl]acetate hydrochloride

Product 1

HCID 53817827{3-[(Propane-1-sulfonylamino)-methyl]-phenyl}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Following the procedure described in Preparation 8, (3-aminomethyl-phenyl)-acetic acid methyl ester hydrochloride (603 mg, 2.80 mmol) was converted to the title sulfonamide by reaction with 1-propanesulfonyl chloride (0.375 mL) and N,N-diisopropylethylamine (2.0 mL) in dichloroethane (10 mL). 1H NMR (400 MHz, CDCl3) δ 7.35-7.22 (m, 4H), 4.60 (bs, 1H), 4.29 (s, 2H), 3.70 (s, 3H), 3.63 (s, 2H), 2.92 (t, 2H), 1.79 (m, 2H), 0.99 (t, 3H).

Sources & evidence

ORD record
ord-dd46717f17b74dedb19d36b94bd61871
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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