Triethylamine → L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)
Reaction equation
[Cl:1]C1C=CC(OC)=C([C@@]2(F)C3C(=CC(C(F)(F)F)=CC=3)N(C([NH:23][C@@H:24]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=O)C2=O)C=1.C(N(CC)CC)C>>[ClH:1].[C:28]([O:27][C:25](=[O:26])[C@H:24]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[NH2:23])([CH3:31])([CH3:29])[CH3:30]Participants
Procedure
(S)-tert-butyl 2-((S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)-3-phenylpropanoate (XVIII7): Following general procedure (F), after forming the intermediate, L-phenylalanine t-butyl ester hydrochloride (0.394 g, 1.53 mmol) and triethylamine (0.41 mL, 2.92 mmol) were added. After work-up and purification, 0.343 g of the title compound as a white foam solid was obtained (42% yield). mp: 62–66° C. MS: 607 (MH+). Anal. Calcd. for C29H25ClF4N2O5.0.5H2O: C, 58.49; H, 4.58; N, 4.55. Found: C, 58.47; H, 4.57; N, 4.28. 1H NMR (CDCl3): δ 1.46 (s, 9H), 3.13 (dd, J=14.0 Hz, 7.6 Hz, 1H), 3.30 (dd, J=14.0 Hz, 5.6 Hz, 1H), 3.34 (s, 3H), 4.80 (m, 1H), 6.74 (dd, J=8.8 Hz, 1.3 Hz, 1H), 7.20–7.27 (m, 6H), 7.36 (dd, J=8.7 Hz, 2.6 Hz, 1H), 7.41 (d, J=7.9 Hz, 1H), 7.78 (dd, J=2.5 Hz, 0.8 Hz, 1H), 8.57 (s, 1H), 8.68 (d, J=7.4 Hz, 1H). IR (KBr, cm−1): 3332, 2980, 1763, 1737, 1716, 1521, 1491, 1439, 1367, 1319, 1262, 1171, 1131, 1061.
Sources & evidence
- ORD record
- ord-0e0c075aee084aaf8b4f20a08ca7e8a2
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169803B2
Reaction notes
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