(Trifluoromethyl)boronic acid → HCID 58717681, compound
Reaction equation
C[O:2][C:3](=[O:37])[C@@H:4]([NH:19][C:20](=[O:36])[C:21]1[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])=[CH:8][CH:7]=1.[F:38][C:39](B(O)O)([F:41])[F:40]>>[Br:27][C:25]1[CH:24]=[CH:23][C:22]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[C:21]([CH:26]=1)[C:20]([NH:19][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:6]2[CH:11]=[CH:10][C:9]([C:39]([F:41])([F:40])[F:38])=[CH:8][CH:7]=2)=[CH:8][CH:7]=1)[C:3]([OH:2])=[O:37])=[O:36]Participants
Procedure
5-Bromo-2-heptyloxy-benzoic acid (0.231 g, 0.738 mmol) and the (2S)-Amino-3-(2′-hydroxy-biphenyl-4-yl)-propionic acid methyl ester (0.200 g, 0.738 mmol) were then combined as per general procedure A with HBTU (0.335 g, 0.885 mmol) and diisopropylethylamine (0.285 g, 2.21 mmol) to yield the (2S)-(5-Bromo-2-heptyloxy-benzoylamino)-3-(2′-hydroxy-biphenyl-4-yl)-propionic acid methyl ester (0.200 g). The methyl ester of the title compound was the prepared from (2S)-(5-Bromo-2-heptyloxy-benzoylamino)-3-(2′-hydroxy-biphenyl-4-yl)-propionic acid methyl ester (0.080 g, 0.140 mmol) and the trifluoromethylboronic acid (0.050 g, 0.281 mmol) as per general procedure F, which was further hydrolyzed as per general procedure C to give the title compound (0.020 g). 1H-NMR(400 MHz, CDCl3): 1.14(t, 3H), 1.53 (m, 8H), 1.92(m, 2H), 3.6(m, 2H), 4.21(m, 2H), 5.21(m, 1H), 7.12(d, 1H), 7.22(m, 2H), 7.36(d, 1H), 7.5(d, 2H), 7.58(m, 2H), 7.66(m, 1H), 7.78 (m, 6H), 8.62 (S, 1H), 8.9 (bs, 1H).
Sources & evidence
- ORD record
- ord-57e9e77489ec4e9f97cbf022e24b203e
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07459472B2
Reaction notes
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