Hydrochloric Acid → (2S,4S)-1-(tert-butoxycarbonyl)-4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)pyrrolidine-2-carboxylic acid

HRID 420090Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

Compound 132 (20 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 133 (20.57 g) as a yellow form in 99% yield and 96-97% purity.

Workup

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

Sources & evidence

ORD record: ord-58680a4eec6045f39cce9f3ce0cfa9e9
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093379B2

Reaction notes

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