Triethylamine → Tert-butyl 3-aminopropanoate hydrochloride

HRID 1375737Notes

Reaction equation

[Cl:1]C1C=CC(OC)=C([C@@]2(F)C3C(=CC(C(F)(F)F)=CC=3)N(C([NH:23][CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=O)C2=O)C=1.C(N(CC)CC)C>>[ClH:1].[C:29]([O:28][C:26](=[O:27])[CH2:25][CH2:24][NH2:23])([CH3:32])([CH3:31])[CH3:30]

Participants

Reactant 2

HCID 8471Triethylamine

HCID 86760371HCID 86760371, compound

Product 1

HCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideYield 65%

Procedure

(S)-tert-butyl 3-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)propanoate (XVIII8): Following general procedure (F), after forming the intermediate, β-alanine t-butyl ester hydrochloride (0.278 g, 1.53 mmol) and triethylamine (0.41 mL, 2.92 mmol) were added. After work-up and purification, 0.48 g of the title compound as a white foam solid was obtained (65% yield). mp: 50–53° C. MS: 531 (MH+). Anal. Calcd. for C24H23ClF4N2O5: C, 54.30; H, 4.37; N, 5.28. Found: C, 54.21; H, 4.44; N, 5.25. 1H NMR (CDCl3): δ 1.46 (s, 9H), 2.60 (t, J=6.2, 2H), 3.53 (s, 3H), 3.70 (m, 2H), 6.77 (d, J=8.7 Hz, 1H), 7.25 (m, 1H), 7.36 (dd, J=8.8 Hz, 2.6 Hz, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.79 (d, J=2.2 Hz, 1H), 8.56 (t, J=5.6 Hz, 1H), 8.63 (s, 1H). IR (KBr, cm−1): 3351, 2981, 1762, 1721, 1531, 1491, 1439, 1319, 1261, 1171, 1130, 1060.

Sources & evidence

ORD record: ord-3d9e798a8d144c59b9279c0b551992d7
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169803B2

Reaction notes

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