Lithium Hydroxide → HCID 178443426, compound

Reaction equation

[CH2:1]([O:11][C:12]1[CH:30]=[CH:29][C:15]([C:16]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([O:23]CC)=[O:22])=[O:17])=[CH:14][C:13]=1[CH2:31][C:32]1[NH:36][N:35]=[N:34][N:33]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Li+]>CC(C)=O.O>[CH2:1]([O:11][C:12]1[CH:30]=[CH:29][C:15]([C:16]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([OH:23])=[O:22])=[O:17])=[CH:14][C:13]=1[CH2:31][C:32]1[NH:36][N:35]=[N:34][N:33]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Procedure

A mixture of 580 mg of the product from Example 2 and 280 mg of lithium hydroxide in 10 ml of acetone and 1 ml of water were stirred for 6 hours. The mixture was concentrated in vacuo and the resulting residue was partitioned between diethyl ether and water. The layers were separated and the aqueous layer was extracted with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and concentrated to dryness. The residue was crystallized from hexane/ethyl acetate to provide 47 mg of the title product, m.p. 147°-150° C.