Lithium hydroxide, monohydrate → (R)-3-(3-Cyclopentyl-N-methylpropanamido)-2,3-dihydro-1H-indene-5-carboxylic acid
반응식
[CH:1]1([CH2:6][CH2:7][C:8]([N:10]([C@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([O:23]C)=[O:22])[CH:19]=3)[CH2:14][CH2:13]2)[CH3:11])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O>CO.C1COCC1.O>[CH:1]1([CH2:6][CH2:7][C:8]([N:10]([C@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([OH:23])=[O:22])[CH:19]=3)[CH2:14][CH2:13]2)[CH3:11])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1참가 물질
4
반응물 2
생성물 1
시약·촉매·용매 1
실험 절차
(R)-Methyl 3-(3-cyclopentyl-N-methylpropanamido)-2,3-dihydro-1H-indene-5-carboxylate (B-80) (1.5 g, 4.56 mmol, 1.0 eq.) was dissolved in MeOH:THF:H2O (1:1:1, 24 ml); LiOH H2O (383 mg, 9.118 mmol, 2.0 eq.) was added at 0° C., and the mixture was stirred for 4 hours at RT. After monitoring by TLC, the reaction solution was concentrated under reduced pressure, and the residue was taken up in water (15 ml) and extracted with ethyl acetate (2×20 ml). The aqueous phase was adjusted to pH 1-2 with 3 M HCl solution and extracted with DCM (3×50 ml). The combined org. phases were washed with sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure, dried. The crude product was used in the next stage without being purified further. Yield: 83% (1.2 g, 0.415 mmol)