1-Azetidinesulfonamide → 3-((4-((Azetidin-1-ylsulfonyl)carbamoyl)-2-cyclopropyl-5-fluorophenoxy)-methyl)adamantan-1-yl 2,2,2-trifluoroacetate
Reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[CH:26]1([C:29]2[C:30]([O:39][CH2:40][C:41]34[CH2:50][CH:45]5[CH2:46][CH:47]([CH2:49][C:43]([O:51][C:52](=[O:57])[C:53]([F:56])([F:55])[F:54])([CH2:44]5)[CH2:42]3)[CH2:48]4)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34](O)=[O:35])[CH2:28][CH2:27]1.C([CH:60]1[CH2:63][N:62]([S:64]([NH2:67])(=[O:66])=[O:65])[CH2:61]1)#N.N1(S(N)(=O)=O)CCC1>>[F:56][C:53]([F:54])([F:55])[C:52]([O:51][C:43]12[CH2:49][CH:47]3[CH2:46][CH:45]([CH2:50][C:41]([CH2:40][O:39][C:30]4[CH:31]=[C:32]([F:38])[C:33]([C:34](=[O:35])[NH:67][S:64]([N:62]5[CH2:63][CH2:60][CH2:61]5)(=[O:66])=[O:65])=[CH:37][C:29]=4[CH:26]4[CH2:27][CH2:28]4)([CH2:48]3)[CH2:42]1)[CH2:44]2)=[O:57]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in Example 230 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-cyclopropyl-2-fluoro-4-((3-(2,2,2-trifluoroacetoxy)adamantan-1-yl)methoxy)benzoic acid and to replace 3-cyanoazetidine-1-sulfonamide with azetidine-1-sulfonamide, the title compound was obtained as colorless solid (0.22 g, 47%): 1H NMR (300 MHz, DMSO-d6) δ 11.62 (s, 1H), 7.17 (d, J=8.3 Hz, 1H), 6.95 (d, J=12.9 Hz, 1H), 4.05 (t, J=7.7 Hz, 4H), 3.79 (s, 2H), 2.32 (br s, 2H), 2.19-2.14 (m, 8H), 2.06-2.00 (m, 1H), 1.70-1.59 (m, 6H), 0.95-0.88 (m, 2H), 0.70-0.65 (m, 2H); MS (ES+) m/z 575.1 (M+1); MS (ES−) m/z 573.1 (M−1).
Sources & evidence
- ORD record
- ord-5509d65ac7e14edcb022cd3ed866a528
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
Loading…