Ammonia → HCID 11281273, compound
Reaction equation
C([N:3](CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]([OH:35])/[CH:17]=[CH:18]/[C@H:19]2[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[N:20]2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][C:32](O)=[O:33])[CH:12]=[CH:13][CH:14]=1.ClC(OCC)=O.N.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]([OH:35])/[CH:17]=[CH:18]/[C@H:19]2[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[N:20]2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][C:32]([NH2:3])=[O:33])[CH:12]=[CH:13][CH:14]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Triethylamine (8.8 μL, 0.063 mmol) was added to a solution of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-hydroxy-but-1-enyl]-6-oxo-piperidin-1-yl}-butoxy)-acetic acid (12.4 mg, 0.030 mmol) in CH2Cl2 (0.2 mL). After cooling to 0° C., the reaction mixture was treated with ethyl chloroformate (3.2 μL, 0.033 mmol). After 1 h at 0° C., ammonia (0.5 M in 1,4-dioxane, 0.32 mL, 0.16 mmol) was added and the reaction mixture was allowed to warm to rt. After 18 h at rt, the reaction mixture was treated with saturated aqueous NaHCO3 (5 mL) and extracted with CH2Cl2 (3×5 mL). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (5% →20% MeOH/CH2Cl2, gradient) afforded 1.3 mg (11%) of the title compound.
Workup
- temperatureto warm to rt
- waitAfter 18 h at rt
- extractionextracted with CH2Cl2 (3×5 mL)
- dry with materialThe combined extracts were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification of the residue by flash column chromatography on silica gel (5% →20% MeOH/CH2Cl2, gradient)
Sources & evidence
- ORD record
- ord-165d5f2959194592b93dbc30dcedae05
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179820B2
Reaction notes
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