Sodium Hydroxide → 3-[9-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:27]4[O:26][CH2:25][CH2:24][N:23]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:27]4[O:26][CH2:25][CH2:24][N:23]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Ethyl 3-[9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate (Preparation 91) (28 mg, 0.058 mmol) was dissolved in ethanol (5 ml). 2M sodium hydroxide (0.144 ml, 0.288 mmol) was added and the reaction mixture stirred at 60° C. for 4 hours. The solvent was evaporated and the reaction mixture diluted with water, neutralised with 2M hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to give the product as a white solid (26 mg).
Workup
- customThe solvent was evaporated
- additionthe reaction mixture diluted with water
- extractionextracted with ethyl acetate
- washThe organic phase was washed with water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-e38f0ab6f1744f31b15bd97db2c64606
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222245B2
Reaction notes
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