Ethyl L-valinate hydrochloride → HCID 10712597, compound

HRID 1794806Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl.[CH2:18]([O:20][C:21](=[O:27])[C@H:22]([CH:24]([CH3:26])[CH3:25])[NH2:23])[CH3:19]>>[CH2:18]([O:20][C:21](=[O:27])[C@@H:22]([NH:23][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([N:5]2[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][CH2:6]2)=[CH:16][CH:15]=1)[CH:24]([CH3:26])[CH3:25])[CH3:19]

Participants

Reactant 2

HCID 87181Ethyl L-valinate hydrochloride

HCID 220640224-(4-Oxopiperidin-1-yl)benzoic acid

Product 1

HCID 10712597HCID 10712597, compound

Procedure

The title compound was prepared from 4-(4-oxo-piperidin-1-yl)-benzoic acid (which was obtained in Example 151) and L-valine ethyl ester hydrochloride according to the procedure of Example 154 as a pale yellowish solid; 1H NMR (300 MHz, DMSO-d6) δ 0.93 (d, J=6.8 Hz, 3 H), 0.97 (d, J=6.8 Hz, 3 H), 1.20 (t, J=7.1 Hz, 3 H), 2.10–2.30 (m, 1 H), 2.43 (t, J=6.0 Hz, 4 H), 3.72 (t, J=6.0 Hz, 4 H), 4.00–4.30(m, 4 H), 4.46 (t, J=5.1 Hz, 1 H), 7.05 (d, J=8.9 Hz, 2 H), 7.82(d, J=8.9 Hz, 2 H), 8.21 (d, J=7.9 Hz, 1 H); MS (ES) m/z: 347.3 (MH+); HRMS Calcd. for C19H26N2O4(M+): 346.1892. Found: 346.1896.

Sources & evidence

ORD record: ord-c257bf386cef4b25a72c8a1e52469384
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022716B2

Reaction notes

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