Methanesulfonamide → HCID 76169163, compound

HRID 2181122Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([C:17](=[O:27])[CH:18]=[C:19]2[C:23](=O)[O:22]C(C)(C)[O:20]2)[O:15][CH3:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][S:30]([NH2:33])(=[O:32])=[O:31]>>[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([C:17](=[O:27])[CH:18]=[C:19]([OH:20])[C:23]([NH:33][S:30]([CH3:29])(=[O:32])=[O:31])=[O:22])[O:15][CH3:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 72879Methanesulfonamide

HCID 74058496HCID 74058496, compound

Product 1

HCID 76169163HCID 76169163, compoundYield 67%

Procedure

Reaction of 4-({[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl]-methoxy-amino}-methyl)-benzoic acid tert-butyl ester (0.060 g, 0.15 mmol) with methanesulfonamide (0.014 g, 0.15 mmol) as described in the prepartion of compound 22 gave 0.043 g (67% yield) of the title amide as a white solid. 1H NMR (400 MHz, CDCl3) δ: mixture of rotamers: 1.58 (9H, s t-Bu), 3.31, 3.33 and 3.36 (3H, 3 S, SO2CH3), 3.61, 3.66 and 3.70 (3H, 3 s, OCH3), 4.8 and 4.88 (2H, 2 s, NCH2), 6.6 (1H, s, CH), 7.28 (2H, m, aromatics), 7.98 (2H, m, aromatics), 8.98 (1H, broad s, NH). HRMS (ESI/neg) calculated for C18H23N2O8S: [M−H]−: 427.117513; found: 427.117342.

Sources & evidence

ORD record: ord-5fdf9f81837a463dac6ea354450160be
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890942B2

Reaction notes

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