Methanesulfonamide → 3-Hydroxy-4-methanesulfonylamino-4-oxo-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amide

Participants

Role	Name	HCID	Charge
Reactant	Methanesulfonamide	HCID 72879	—
Reactant	2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide	HCID 73033233	—
Product	3-Hydroxy-4-methanesulfonylamino-4-oxo-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amide	HCID 72613056	29%

Reaction Steps

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide was treated with methane sulfonamide as described in the preparation of compound 1 to yield 100 mg solid (29% yield), mp=137° C. (decomposition). HRMS (M−H) cacld for C13H14FN2O6S: 345.056. Found: 345.0570. Anal calcd for C13H15FN2O6S: C, 45.08; H, 4.36; N, 8.08. Found: C, 45.20; H, 4.29; N, 7.92. 1H NMR (500 MHz, CDCl3) δ: 3.36 (s, 3), 3.71 (s, 3), 4.81 (s, 2), 6.56 (s, 1), 7.04 (m, 2), 7.32 (m, 2), 8.97 (s, 1). 13C NMR (125 MHz, CDCl3) δ: 41.60, 48.27, 63.16, 92.57, 115.65, 115.81, 130.19, 130.24, 130.97, 158.99, 160.05, 161.65, 163.61, 170.79.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06890942B2
Source dataset	uspto-grants-2005_05
ORD ID	ord-538fa56047574cea89365fdc1f8c4726
Source note	uspto-grants-2005_05