Lithium hydroxide, monohydrate → HCID 69820413, compound

Reaction equation

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

Participants

Procedure

A mixture of 3.55 g (8.0 mmol) of methyl (S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[(phenylmethoxy)carbonyl]piperidine-4-pentanoate and 0.40 g (9.6 mmol) of lithium hydroxide monohydrate in 15 ml of methanol and 5 ml of water is stirred for 18 h at room temperature. The methanol is evaporated off under reduced pressure and the mixture is then cooled to 0° C. and acidified to pH 2 with aqueous 1N hydrochloric acid solution, and then extracted twice with 150 ml of ethyl acetate. The resulting extract is washed with 100 ml of saturated sodium chloride solution and then dried over sodium sulphate and filtered, and the residue obtained is concentrated. 3 g of (S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[(phenylmethoxy)carbonyl]piperidine-4-pentanoic acid are obtained in the form of a white powder, which is used without further purification in the following step.