Lithium Hydroxide → HCID 70976581, compound

HRID 572350Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[OH-].[Li+:33]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O-:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[Li+:33]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of methyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 19) (1.63 g, 3.84 mmol) in methanol (20 mL) was added lithium hydroxide (4.61 mL, 4.61 mmol). The resulting mixture was stirred at 40° C. for 6 h, whereupon it was concentrated under reduced pressure to give lithium 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (1.65 g, 100%) which was not purified but directly used in the subsequent step. LCMS (Formate, 2 min), Rt=0.87, MH+=411.

Workup

concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-429753e44e0b4d06b3a9a5df1594ebb1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029395B2

Reaction notes

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