Methanesulfonamide → HCID 86591196, compound

HRID 983902Notes

Reaction equation

HRID 983902 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:27](=[O:28])[N:26]2[CH:22]([CH2:23][CH:24]([O:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=[CH:32][CH:31]=3)[CH2:25]2)[C:21](=[O:40])[NH:20][C:19]2([C:41](O)=[O:42])[CH:17]([CH2:18]2)[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:44][S:45]([NH2:48])(=[O:47])=[O:46]>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[C:27](=[O:28])[N:26]2[C@@H:22]([CH2:23][C@@H:24]([O:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=[CH:32][CH:31]=3)[CH2:25]2)[C:21](=[O:40])[NH:20][C@@:19]2([C:41]([NH:48][S:45]([CH3:44])(=[O:47])=[O:46])=[O:42])[C@@H:17]([CH2:18]2)[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 72879MethanesulfonamideHCID 72995270HCID 72995270, compound

Product 1

HCID 86591196HCID 86591196, compoundYield 20%

Procedure

(1S,4R,6S,14S,18R)-7-cis-[14-tert-butoxycarbonylamino-2,15-dioxo-18-(quinolin-4-yloxy)-3,16-diaza tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid, the product of Step F in Example 30 (50 mg, 0.075 mmol) was reacted in analogous fashion with methanesulfonamide (12 mg, 0.12 mmol) as described in the preceding procedure above to give 10 mg (20%) of (1S,4R,6S,14S,18R)-7-cis-[4-methanesulfonylaminocarbonyl-2,15-dioxo-18-(quinolin-4-yloxy)-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-en-14-yl]-carbamic acid tert-butyl ester as a white solid: 1H NMR (300 MHz, CDCl3) δ 1.26 (s, 9H), 1.22-1.94 (m, 11H), 2.27 (m, 1H), 2.55 (m, 1H), 2.67 (m, 2H), 3.17 (s, 3H), 4.05 (m, 1H), 4.27 (m, 1H), 4.61 (t, J=8.1 Hz, 1H), 4.73 (d, J=11.0 Hz, 1H), 4.96-5.02 (m, 2H), 5.35 (s, 1H), 5.71 (q, J=8.8 Hz, 1H), 6.73 (d, J=5.1 Hz, 1H), 6.93 (bs, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.69 (t, J=7.7 Hz, 1H), 8.06 (d, J=8.8 Hz, 1H), 8.15 (d, J=7.7 Hz, 1H), 8.77 (d, J=5.5 Hz, 1H). LC-MS (Method A, retention time: 2.43 min), MS m/z 670 (M++1). Preparation of Example 32, 2(S)-tert-butoxycarbonylamino-3-pentenylsulfanylpropionic acid methyl ester (Example 32) for use in Example 33.

Sources & evidence

ORD record
ord-7089c2f438ba4390b69f936fd9984832
Source dataset
uspto-grants-2005_03
Patent number
US06867185B2

Reaction notes

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