Triethylamine → L-Aspartic acid, bis(1,1-dimethylethyl) ester, hydrochloride

HRID 1375732Notes

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]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[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]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[NH2:23])([CH3:30])([CH3:31])[CH3:29]

Participants

Reactant 2

HCID 8471Triethylamine

HCID 86760367(S)-di-tert-butyl 2-((S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)succinate

Product 1

HCID 13768146L-Aspartic acid, bis(1,1-dimethylethyl) ester, hydrochlorideYield 50%

Procedure

(S)-di-tert-butyl 2-((S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)succinate (XVIII2): Following general procedure (F), after forming the intermediate, (L)-Aspartic acid di-t-butyl ester hydrochloride (0.391 g, 1.39 mmol) and triethylamine (0.39 mL, 2.78 mmol) were added. After work-up and purification, 0.44 g of the title compound as white foam solid was obtained (50% yield). mp: 63–66° C. MS: 631 (MH+). Anal. Calcd. for C29H31ClF4N2O7: C, 55.20; H, 4.95; N, 4.44. Found: C, 55.07; H, 4.63; N, 4.27. 1H NMR (CDCl3): δ 1.44 (s, 9H), 1.51 (s, 9H), 2.87 (dd, J-16.8 Hz, 4.8 Hz, 1H), 3.01 (dd, J=16.8 Hz, 4.8 Hz, 1H), 3.52 (s, 3H), 4.78 (dt, J=7.8 Hz, 4.7 Hz, 1H), 6.75 (dd, J=8.8 Hz, 1.2 Hz, 1H), 7.25 (m, 1H), 7.35 (dd, J=8.7 Hz, 2.6 Hz, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.80 (dd, J=2.6 Hz, 0.9 Hz, 1H), 8.6 (s, 1H), 9.02 (d, J=7.7 Hz, 1H). IR (KBr, cm−1): 3338, 2982, 2942, 1766, 1733, 1520, 1491, 1440, 1319, 1262, 1170, 1132.

Sources & evidence

ORD record: ord-15da886bbb6044ce928491167d5c7e6f
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169803B2

Reaction notes

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