Hydrochloric Acid → HCID 67773516, compound
Reaction equation
[CH:1]1([CH2:7][NH:8][C:9]([C@@H:11]2[CH2:15][C@@H:14]([OH:16])[CH2:13][NH:12]2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(=O)([O-])[O-].[K+].[K+].Br[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1.C(N(CC)CC)C>[Br-].C([N+](CC)(CC)CC)C.C(OCC)(=O)C.[Cu](I)I.O.CN(C)C=O>[CH:1]1([CH2:7][NH:8][C:9]([C@@H:11]2[CH2:15][C@@H:14]([OH:16])[CH2:13][N:12]2[C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 100 °C
Procedure
A mixture of (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid cyclohexylmethyl-amide; hydrochloride (75 mg, 0.285 mmol), dichlorobis(tri-o-tolylphosphine) palladium (II) (11 mg, 0.014 mmol), copper iodide (2.7 mg, 0.014 mmol), potassium carbonate (78.8 mg, 0.57 mmol), tetraethylammonium bromide (10.2 mg, 0.048 mmol) and 2-bromo-5-trifluoromethylpyridine (64.4 mg, 0.285 mmol) is evacuated and filled with Argon three cycles. Triethylamine (0.16 mL, 1.14 mmol), N,N-dimethylformamide (1 mL) and water (0.1 mL) are added and the reaction mixture is heated to 100° C. under Argon atmosphere for 22 h. The reaction is diluted with ethyl acetate and concentrated. The residue is purified by flash chromatography on silica eluting with methanol/dichloromethane which provides the title compound, m/z 372 [M+H+].
Workup
- additionfilled with Argon three cycles
- concentrationconcentrated
- customThe residue is purified by flash chromatography on silica eluting with methanol/dichloromethane which
Sources & evidence
- ORD record
- ord-c8d7a360c8db4dd0bf9614ec659d41bc
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629157B2
Reaction notes
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