Boc-L-Pro-Ome → (2S)-(1-tert-Butoxycarbonyl-2-pyrrolidinyl)2,8-bis(trifluoromethyl)quinolin-4-yl Methanone
Reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.C[O:21][C:22](=O)[C@@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>>[C:31]([O:30][C:28]([N:24]1[CH2:25][CH2:26][CH2:27][C@H:23]1[C:22]([C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1)=[O:21])=[O:29])([CH3:34])([CH3:33])[CH3:32]Participants
3
Procedure
This was prepared from 4-bromo-2,8-bis(trifluoromethyl)quinoline by the method of example 31 using (S)-N-tert-butoxycarbonylproline methyl ester in place of N-diphenylmethyl-3-azetidinone and the product (1.32 g, 29%) isolated as a cream solid: IR νmax (Nujol)/cm−1 2979, 2883, 1748, 1698, 1401, 1368, 1312, 1160 and 1110; NMR δH (400 CDCl3) (mixture of 2 rotamers) 1.41 and 1.45 (9H, 2×s), 1.79-2.13 (3H, m), 2.11-2.31 (1H, m), 3.32-3.70 (2H, m), 5.09 and 5.16 (1H, 2×dd, J 8.8, 4.3 and J 9.0, 5.5 Hz), 7.78-7.83 (1H, m), 8.03 and 8.04 (1H, 2×s), 8.18-8.29 (1H, m), 8.41 and 8.51 (1H, 2×d, J 8.5 and J 8.5 Hz).
Sources & evidence
- ORD record
- ord-c985aca4dcd74f9c9c263b2440c2c0d1
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06608085B1
Reaction notes
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