Benzoic Acid → benzyl (3R)-4-(5-cyano-2-iodophenoxy)-3-[4-(pyrrolidine-1-carbonyl)benzoylamino]butyrate
Reaction equation
[Cl-].[CH2:2]([O:9][C:10]([CH2:12][C@@H:13]([NH3+:25])[CH2:14][O:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:17]=1[I:24])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:26](O)(=[O:33])[C:27]1[CH:32]=[CH:31]C=[CH:29][CH:28]=1.[OH:35]N1C2C=CC=CC=2N=N1.[CH2:45]([N:47]([CH2:50][CH3:51])[CH2:48][CH3:49])[CH3:46].Cl.CN(C)CCCN=C=NCC>ClCCl.O>[C:22]([C:20]1[CH:19]=[CH:18][C:17]([I:24])=[C:16]([CH:21]=1)[O:15][CH2:14][C@H:13]([NH:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][C:46]([C:45]([N:47]2[CH2:50][CH2:51][CH2:49][CH2:48]2)=[O:35])=[CH:29][CH:28]=1)[CH2:12][C:10]([O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:11])#[N:23]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
2.0 g (4.23 mmol) of (1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethyl ammonium chloride, 1.02 g (4.65 mmol) of 4-pyrrolidine-1-carbonyl)benzoic acid, 630 mg (4.65 mmol) of 1-hydroxybenzotriazole, and 1.30 ml (9.31 mmol) of triethylamine were dissolved in 40 ml of dichloromethane, and 890 mg (4.65 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride was added thereto and stirred under cooling with ice for 10 minutes and then at room temperature for 18 hours. The reaction was stopped by adding water, and the title compound was obtained in an ordinary manner by treatment with dichloromethane as the extractant.
Workup
- temperatureunder cooling with ice for 10 minutes
Sources & evidence
- ORD record
- ord-668648b39abc4945a20eb03e2dccf5a3
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07396844B1
Reaction notes
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