1-(Cyclopropylmethyl)cyclopropane-1-sulfonamide → 4-(1-Cyclopropylmethyl-cyclopropanesulfonylamino)-3-hydroxy-4-oxo-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amide

HRID 2181109Notes

Reaction equation

HRID 2181109 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:11][CH3:12])=[O:9])[C:4](=[O:21])O1.[CH:23]1([CH2:26][C:27]2([S:30]([NH2:33])(=[O:32])=[O:31])[CH2:29][CH2:28]2)[CH2:25][CH2:24]1>>[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8](=[O:9])[CH:7]=[C:5]([OH:6])[C:4]([NH:33][S:30]([C:27]2([CH2:26][CH:23]3[CH2:24][CH2:25]3)[CH2:28][CH2:29]2)(=[O:31])=[O:32])=[O:21])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 224992851-(Cyclopropylmethyl)cyclopropane-1-sulfonamideHCID 730332332-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide

Product 1

HCID 726130754-(1-Cyclopropylmethyl-cyclopropanesulfonylamino)-3-hydroxy-4-oxo-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amide

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide was treated with 1-cyclopropylmethyl-cyclopropanesulfonic acid amide as described in the preparation of compound 1 to yield the title compound. MS (M−H) calcd for C19H22FN2O6S: 425.1. Found: 425.0. 1H NMR (500 MHz, CDCl3) δ: 0.12 (m, 2), 0.50 (m, 2), 0.70 (m, 1), 1.14 (m, 2), 1.75 (m, 2), 1.88 (m, 2), 3.69 (s, 3), 4.79 (s, 2), 6.54 (s, 1), 7.03 (m, 2), 7.30 (m, 2), 8.83 (s, 1). Anal calcd for C19H23FN2O6S; C, 53.51; H, 5.43; N, 6.56. Found: C, 53.43; H, 5.64; N, 6.51.

Sources & evidence

ORD record
ord-cdc273ce88ae42429d0846ebb8cf5211
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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