Trifluoroacetic acid → O-Benzyl-N-Methyl-L-Tyrosinamide
Reaction equation
[CH3:1][NH:2][C:3](=[O:28])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][NH:2][C:3](=[O:28])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:16][CH:15]=1)[NH2:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-Boc-O-benzyl tyrosine methylamide (5.29 g, 13.8 mmol) was taken up in CH2Cl2 (100 ml). To the solution at 0° C. TFA (10 ml) was added dropwise and the solution allowed to warm to ambient temperature. After 4 hours the solvent and TFA were removed under vacuum. Any remaining TFA was quenched with saturated NaHCO3 solution (100 ml). The reaction mixture was extracted using CH2Cl2 (100 ml) and washed with saturated NaHCO3 solution (100 ml) and brine (100 ml). The CH2Cl2 layer was dried over Na2SO4 and the solvent was removed under vacuum to give a white solid, which was recrystallised from ethyl acetate/hexane to yield the title compound as a white crystalline solid (3.35 g, 85.4%).
Workup
- customat 0° C
- customAfter 4 hours the solvent and TFA were removed under vacuum
- customAny remaining TFA was quenched with saturated NaHCO3 solution (100 ml)
- extractionThe reaction mixture was extracted
- washwashed with saturated NaHCO3 solution (100 ml) and brine (100 ml)
- dry with materialThe CH2Cl2 layer was dried over Na2SO4
- customthe solvent was removed under vacuum
- customto give a white solid, which
- customwas recrystallised from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-f88abcc75e4b40fc80203379176ec462
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05300674
Reaction notes
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