Methylamine → (S)-2-(5-bromo-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyethyl pivalate

HRID 931748Notes

Reaction equation

[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:16]([Br:30])=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[N:21]=[C:20]([O:26]C(=O)C)[CH:19]=[CH:18]2)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CN>C(O)C>[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:16]([Br:30])=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[NH:21][C:20](=[O:26])[CH:19]=[CH:18]2)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 78 °C

Procedure

To the solution of (S)-2-(2-acetoxy-5-bromo-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate (130 mg) in ethanol (7.5 mL) was added aqueous methylamine solution (0.5 mL, 50%). The mixture was heated at 78° C. for 80 min. Concentration and purification gave (S)-2-(5-bromo-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyethyl pivalate (68 mg). LCMS-ESI+ (m/z): 438.2, 440.2 (M+H)+.

Workup

concentrationConcentration and purification

Sources & evidence

ORD record: ord-2fd31e5ecc904a5ea0b2df79d4deaa57
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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