O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:49]=[C:48]([O:50][CH3:51])[CH:47]=[CH:46][C:7]=1[CH2:8][NH:9][C:10]1[C:11]2[CH:18]=[CH:17][N:16]([C@H:19]3[C@@H:23]4[O:24][C:25]([CH3:28])([CH3:27])[O:26][C@@H:22]4[C@@H:21]([CH2:29][N:30]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH:31]4[CH2:34][CH:33]([CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])[CH2:32]4)[CH2:20]3)[C:12]=2[N:13]=[CH:14][N:15]=1.O1CCCC1.CO.Cl>>[CH3:4][O:5][C:6]1[CH:49]=[C:48]([O:50][CH3:51])[CH:47]=[CH:46][C:7]=1[CH2:8][NH:9][C:10]1[C:11]2[CH:18]=[CH:17][N:16]([C@H:19]3[C@@H:23]4[O:24][C:25]([CH3:27])([CH3:28])[O:26][C@@H:22]4[C@@H:21]([CH2:29][N:30]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH:31]4[CH2:32][CH:33]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])[CH2:34]4)[CH2:20]3)[C:12]=2[N:13]=[CH:14][N:15]=1Lithium hydroxide, monohydrate (1.11 g, 26.4 mmol) was added to a solution ethyl 3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isobutyl)amino)cyclobutyl)propanoate (1.75 g, 2.64 mmol) in Tetrahydrofuran (13 ml, 160 mmol) and Methanol (3 ml, 70 mmol). The reaction was stirred for 24 hours at RT, acidified with 1 N HCl to pH=6, the volatiles removed in vacuo and remaining water removed by azeotropic distillation with ethanol followed by 18 hours on lyophilizer. The resulting off white solid was used without further purification.
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