Acetic Acid → HCID 89590898, compound
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C@H:10]1[C:43](=[O:44])[N:42]2[CH2:45][C@@H:39]([CH2:40][C@H:41]2[C:46]([O:48]C)=[O:47])[O:38][C:22]2=[N:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]([O:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]2[CH2:50][C@H:14]2[O:13][C:12](=[O:51])[NH:11]1.O.[OH-].[Li+].C(O)(=O)C.O>CO.C1COCC1>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C@H:10]1[C:43](=[O:44])[N:42]2[CH2:45][C@@H:39]([CH2:40][C@H:41]2[C:46]([OH:48])=[O:47])[O:38][C:22]2=[N:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]([O:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:36])[CH3:37])=[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]2[CH2:50][C@H:14]2[O:13][C:12](=[O:51])[NH:11]1Participants
7
Procedure
A solution of the product of step 6 (210 mg, 0.300 mmol) in MeOH (3005 μl), THF (1502 μl) and eater (1502 μl) was treated with lithium hydroxide monohydrate (63.0 mg, 1.502 mmol). The reaction mixture was stirred at room temperature. After 5 hour the reaction was quenched by addition of acetic acid (172 μl, 3.00 mmol) and water (10 mL). The mixture was extracted into dichloromethane (2×10 mL) and ethyl acetate (10 mL). The combined organic extracts were dried over magnesium sulfate filtered and concentrated in rotavap to give the title compound (215 mg, 0.314 mmol, 104% yield) as a white powder. No further purification was carried out for the product.
Workup
- extractionThe mixture was extracted into dichloromethane (2×10 mL) and ethyl acetate (10 mL)
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in rotavap
Sources & evidence
- ORD record
- ord-3fb451a661e34fb3931a3d976c2c83ad
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328138B2
Reaction notes
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