Methanol → (R)-3,3-dimethyl-2-(6-methyl-3-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)butanoic acid

HRID 1968292Notes

Reaction equation

[CH3:1][C:2]([CH3:32])([CH3:31])[C@@H:3]([N:7]1[C:16](=[O:17])[C:15]2=[CH:18][N:19](S(C3C=CC(C)=CC=3)(=O)=O)[C:13]3[C:14]2=[C:9]([C:10]([CH3:30])=[CH:11][N:12]=3)[CH2:8]1)[C:4]([OH:6])=[O:5].CO.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]([CH3:32])([CH3:31])[C@@H:3]([N:7]1[C:16](=[O:17])[C:15]2=[CH:18][NH:19][C:13]3[C:14]2=[C:9]([C:10]([CH3:30])=[CH:11][N:12]=3)[CH2:8]1)[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

(R)-3,3-Dimethyl-2-(6-methyl-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)butanoic acid (36 mg, 0.079 mmol)) was dissolved in THF (3 mL), MeOH (3 mL) and aqueous NaOH (1N, 3 mL) in a 50 mL round bottom flask. The reaction mixture was heated at 50° C. for 30 min in an oil bath then cooled to room temperature. The solution was concentrated and purified by preparative HPLC (10-35% AcCN/H2O with 0.035% TFA) to give the title compound (10 mg, 42%). 1H NMR (500 MHz, CD3OD) δ 1.25 (s, 9H), 2.29 (s, 3H), 4.87 (s, 1H), 5.21 (d, J=19.5 Hz, 1H), 5.37 (d, J=19.5 Hz, 1H), 7.87 (s, 1H), 8.23 (s, 1H). [M+H] calc'd for C16H19N3O3, 302; found, 302.

Workup

temperaturethen cooled to room temperature
concentrationThe solution was concentrated
custompurified by preparative HPLC (10-35% AcCN/H2O with 0.035% TFA)

Sources & evidence

ORD record: ord-a40bd93b612c47b2b7b45d8a736261f5
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420816B2

Reaction notes

Loading…