Hydrochloric Acid → 5-(1-(tert-Butoxycarbonyl)-4-hydroxypyrrolidin-3-yloxy)-2'-cyano-4'-methylbiphenyl-3-carboxylic acid

HRID 1845329Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of tert-butyl 3-(2′-cyano-5-(methoxycarbonyl)-4′-methylbiphenyl-3-yloxy)-4-hydroxypyrrolidine-1-carboxylate (310 mg, 0.68 mmol) in THF (3 mL) was added 2.5 M of aq. lithium hydroxide solution (1.5 mL, 3.8 mmol). The reaction mixture was stirred at 60° C. overnight. The aqueous solution was acidified with 15% HCl (aq.) to pH=5, and extracted with EtOAc. The combined organic layers were concentrated in vacuo to afford the title compound.

Workup

extractionextracted with EtOAc
concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record: ord-7a16284b770d48ec800cf279c076ad21
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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