Methanol → HCID 53924910, compound

Participants

Reaction Conditions

Reaction Steps

A solution of lithium hydroxide monohydrate (35 mg) in water (2 mL) was added to a solution of trans-4-(N-tert-butoxycarbonylamino)-1-(N-tert-butoxycarbonyl-N-methylglycyl)-L-proline methyl ester (E, 289 mg) in tetrahydrofuran (6 mL)-methanol (2 mL) at 0° C. After stirring at 0° C. for 10 min and at room temperature for 15 hr, the solvents were removed in vacuo. The residue was diluted with water and washed with diethyl ether. The aqueous layer was acidified with 1 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to afford the title compound (258 mg) as a colorless oil. The compound appears as a mixture of rotamers: 1H NMR (400 MHz, CDCl3) δ 1.36 (s, 9H), 1.38 (s, 9H), 2.03-2.30 (m, 1.5H), 2.62-2.94 (m, 3.5H), 3.20-4.02 (m, 4H), 4.07-4.42 (m, 1H), 4.46-4.62 (m 1H), 5.24-5.62 (m, 0.5H), 5.70-5.82 (m, 0.5H), and 8.60 (br s, 1H).

Provenance & Evidence