3,5-Bis(trifluoromethyl)benzyl bromide → 2-acetamido-3-(1H-indol-3-yl)propanoic acid [3,5-bis(trifluoromethyl)phenyl]methyl ester
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6]Br.[C:17]([NH:20][C@H:21]([C:32]([OH:34])=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)(=[O:19])[CH3:18]>>[C:17]([NH:20][CH:21]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[C:32]([O:34][CH2:6][C:5]1[CH:4]=[C:3]([C:2]([F:16])([F:15])[F:1])[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=1)=[O:33])(=[O:19])[CH3:18]Participants
3
Procedure
Following the method of Example 1, 3,5-bistrifluoromethylbenzyl bromide (6.16 g) and N acetyl-L-tryptophan (4.92 g) gave the title compound which was recrystallised from ethyl acetate/petroleum ether (3.7 g), m.p. 147°-148° C. 1H NMR (360 MHz, CDCl3) δ8.01 (1H, s), 7.83 (1H, s), 7.61 (1H, s), 7.51 (1H, d, J=8 Hz), 7.32 (1H, d, J=8 Hz), 7.17 (1H, t, J=7 Hz), 7.09 (1H, t, J=7 Hz), 6.91 (1H, d, J=2 Hz), 5.98 (1H, s), 5.13 (1H, d, J=13 Hz), 5.06 (1H, t, J=13 Hz), 4.96 (1H, t, J=6 Hz), 3.31 (2H, m), 1.98 (1H, s); Found: C, 56.08; H, 3.79; N, 5.74. C22H18N2F6O3 requires C, 55.84; H, 3.84; N, 5.93%.
Sources & evidence
- ORD record
- ord-2c4ba570d6f94e94b3830b66476b990b
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05472978
Reaction notes
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