(-)-Myrtanol → 5-chloro-4-(((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methoxy)-2-fluoro-N-(methylsulfonyl)benzamide

HRID 1427802Notes

Reaction equation

HRID 1427802 reaction equation
C1(CCO)CC1.[CH3:7][C:8]1([CH3:17])[C@H:13]2[CH2:14][C@@H:9]1[CH2:10][CH2:11][C@@H:12]2[CH2:15][OH:16].FC1C=C(F)C(F)=CC=1C(NS(C)(=O)=O)=O.[Cl:34][C:35]1[C:36](F)=[CH:37][C:38]([F:48])=[C:39]([CH:47]=1)[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[O:41]>>[Cl:34][C:35]1[C:36]([O:16][CH2:15][C@H:12]2[CH2:11][CH2:10][C@H:9]3[CH2:14][C@@H:13]2[C:8]3([CH3:17])[CH3:7])=[CH:37][C:38]([F:48])=[C:39]([CH:47]=1)[C:40]([NH:42][S:43]([CH3:46])(=[O:44])=[O:45])=[O:41]

Participants

5

Reactant 4

HCID 104476(-)-MyrtanolHCID 1376422-Cyclopropylethan-1-olHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 580424352,4,5-trifluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 867028305-chloro-4-(((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methoxy)-2-fluoro-N-(methylsulfonyl)benzamide

Procedure

Following the procedure as described in Example 1 and making variations as required to replace 2-cyclopropylethanol with ((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]-heptan-2-yl)methanol and 2,4,5-trifluoro-N-(methylsulfonyl)benzamide with 5-chloro-2,4-difluoro-N-(methylsulfonyl)-benzamide, the title compound was obtained as a colorless solid (0.03 g, 2%): 1H NMR (300 MHz, DMSO-d6) δ 12.10 (s, 1H), 7.76 (d, J=7.4 Hz, 1H), 7.25 (d, J=12.5 Hz, 1H), 3.96 (d, J=6.8 Hz, 2H), 3.35 (s, 3H), 2.47-2.37 (m, 1H), 2.10-2.03 (m, 1H), 1.94-1.65 (m, 5H), 1.48-1.37 (m, 2H), 1.12 (s, 3H), 0.85 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.3 (d, J=2 Hz), 159.8 (d, JC-F=255 Hz), 158.1 (d, JC-F=11 Hz), 130.7 (d, JC-F=3 Hz), 116.6 (d, JC-F=3 Hz), 113.7 (d, JC-F=14 Hz), 102.5 (d, JC-F=28 Hz), 73.1, 41.9, 41.2, 40.1, 38.8, 34.1, 26.5, 23.5, 23.1, 20.0, 17.4; MS (ES−) m/z 402.1, 404.1 (M−1).

Sources & evidence

ORD record
ord-e6f31cfbc083448db2e8ec68bb3b7cef
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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