Hydrochloric Acid → (2S,4S)-1-(tert-butoxycarbonyl)-4-(7-methoxy-8-methyl-2-(4-(trifluoromethyl)thiazol-2-yl)quinolin-4-yloxy)pyrrolidine-2-carboxylic acid

HRID 420084Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:23][C@@H:24]3[CH2:28][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:26]([C:36]([O:38]C)=[O:37])[CH2:25]3)=[CH:8][C:9]([C:14]3[S:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=3)=[N:10]2)=[CH:5][CH:4]=1.O.[OH-].[Li+].Cl>C1COCC1>[C:32]([O:31][C:29]([N:27]1[CH2:28][C@@H:24]([O:23][C:7]2[C:6]3[C:11](=[C:12]([CH3:13])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=[C:9]([C:14]3[S:15][CH:16]=[C:17]([C:19]([F:20])([F:22])[F:21])[N:18]=3)[CH:8]=2)[CH2:25][C@H:26]1[C:36]([OH:38])=[O:37])=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

Conditions

Temperature: 40 °C

Procedure

Compound 124 (22.24 g) was dissolved in THF (66 mL) at room temperature. Water (66 mL) was added, followed by lithium hydroxide (5 eq.) in one portion. The reaction mixture was heated at 40° C. for 3 hrs, cooled, acidified with 5M HCl, and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated under vacuum to give compound 125 (21.33 g) as an off-white powder in 92% yield (7.5 w % of THF) and 99% purity.

Workup

temperaturecooled
extractionextracted with DCM
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-48593f16503244d49a10adea45d01674
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093379B2

Reaction notes

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