1,2-Dichloroethane → N2-(tert-butoxycarbonyl)-3-hydroxy-N-(2,2,2-trifluoroethyl)-D-valinamide
Reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[F:18][C:19]([F:23])([F:22])[CH2:20][NH2:21].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl.C(OCC)(=O)C>[C:4]([O:3][C:1]([NH:8][C@@H:9]([C:10]([NH:21][CH2:20][C:19]([F:23])([F:22])[F:18])=[O:12])[C:13]([OH:16])([CH3:15])[CH3:14])=[O:2])([CH3:5])([CH3:6])[CH3:7]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a vial was added (R)—N-Boc-2-amino-3-hydroxy-3-methylbutanoic acid (CA, 500 mg, 2.144 mmol), 2,2,2-trifluoroethanamine hydrochloride (581 mg, 4.29 mmol), EDC (493 mg, 2.57 mmol), and HOBT (328 mg, 2.144 mmol). The reactants were dissolved in DCM (10 mL) and then DIEA (1.497 mL, 8.57 mmol) was added. The mixture was allowed to stir at RT overnight. The mixture was diluted with ethyl acetate, washed 2× with aqueous sodium hydrogen carbonate and 1× with brine. Aqueous layers were back extracted once with ethyl acetate, combined organic layers were dried with Na2SO4, filtered and the solvent was evaporated under reduced pressure. The material I-27a was used directly in the subsequent step without purification.
Workup
- washwashed 2× with aqueous sodium hydrogen carbonate and 1× with brine
- extractionAqueous layers were back extracted once with ethyl acetate
- dry with materialwere dried with Na2SO4
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe material I-27a was used directly in the subsequent step without purification
Sources & evidence
- ORD record
- ord-fdc15f59045d4c0b85560e8fb6b3ce9e
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096598B2
Reaction notes
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