Triethylamine → tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride

HRID 1375734Notes

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]([CH:32]([CH3:34])[CH3:33])[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]([CH:32]([CH3:33])[CH3:34])[NH2:23])([CH3:31])([CH3:30])[CH3:29]

Participants

Reactant 2

HCID 8471Triethylamine

HCID 86760368HCID 86760368, compound

Product 1

HCID 12490702tert-butyl (2S)-2-amino-3-methylbutanoate hydrochlorideYield 52%

Procedure

(S)-tert-butyl 2-((S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)-3-methylbutanoate (XVIII5): Following general procedure (F), after forming the intermediate, L-valine t-butyl ester hydrochloride (0.321 g, 1.53 mmol) and triethylamine (0.41 mL, 2.92 mmol) were added. After work-up and purification, 0.40 g of the title compound as a white foam solid was obtained (52% yield). mp: 56–60° C. MS: 489 (no mother ion). Anal. Calcd. for C26H27ClF4N2O5: C, 55.87; H, 4.87; N, 5.01. Found: C, 55.95; H, 4.89; N, 4.89. 1H NMR (CDCl3): δ 0.99 (d, J=6.9 Hz, 3H), 1.04 (d, J=6.8 Hz, 3H), 1.51 (s, 9H),2.33 (m, 1H), 3.55 (s, 3H), 4.50 (dd, J=8.5 Hz, 4.5 Hz, 1H), 6.78 (dd, J=8.8 Hz, 1.2 Hz, 1H), 7.27 (m, 1H), 7.37 (dd, J=8.7 Hz, 2.6 Hz, 1H), 7.43 (d, J=7.9 Hz, 1H), 7.81 (dd, J=2.6 Hz, 0.9 Hz, 1H), 8.6 (s, 1H), 8.70 (d, J=8.4 Hz, 1H). IR (KBr, cm−1): 3338, 2972, 1761, 1735, 1717, 1531, 1491, 1439, 1319, 1261, 1173, 1132, 1061.

Sources & evidence

ORD record: ord-f0630bbd3bf841589c3aba898105bf3d
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169803B2

Reaction notes

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