Ammonium Hydroxide → (S)-2-(4-((R)-4-(4-fluorophenyl)-4,5-dihydrooxazol-2-yl)phenyl)morpholine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:11][C:12](=[O:25])[C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]3[O:24][CH2:23][CH2:22][NH:21][CH2:20]3)=[CH:15][CH:14]=2)[CH2:9]O)=[CH:4][CH:3]=1.C(N(S(F)(F)F)CC)C.[OH-].[NH4+].CCCCCCC.C(OC(=O)C)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:9][O:25][C:12]([C:13]3[CH:18]=[CH:17][C:16]([C@@H:19]4[O:24][CH2:23][CH2:22][NH:21][CH2:20]4)=[CH:15][CH:14]=3)=[N:11]2)=[CH:6][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
N—((R)-1-(4-Fluorophenyl)-2-hydroxyethyl)-4-((S)-morpholin-2-yl)benzamide (14.4 mg, 0.042 mmol) was dissolved in dichloromethane (0.4 ml) and diethylaminosulfur trifluoride (DAST) (6.74 mg, 0.042 mmol) was added. The reaction mixture was allowed to stir at room temperature for 5 hours. The reaction mixture was poured over crushed ice mixed with 25% ammonium hydroxide solution (10 ml) and the solution was extracted twice with dichloromethane (2×10 ml). The combined organic layer was dried over MgSO4 and evaporated to give a sticky solid. Addition of heptane/ethy lacetate 4:1 and some drops of dichloromethane gave a white solid which was isolated by filtration and dried in vacuo to afford the product as a white solid (5.1 mg, 37%): MS (ISP): 327.2 ([M+H]+).
Workup
- additionThe reaction mixture was poured
- customover crushed ice
- extractionthe solution was extracted twice with dichloromethane (2×10 ml)
- dry with materialThe combined organic layer was dried over MgSO4
- customevaporated
- customto give a sticky solid
- customwas isolated by filtration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-548e8f226ab34186af8e38e2b2f2c9a4
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181230B2
Reaction notes
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