Potassium Carbonate → N-tert-butoxycarbonyl-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

HRID 24627Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1B(O)O.C([O-])([O-])=O.[K+].[K+].[CH3:20][O:21][C:22](=[O:47])[C@H:23]([CH2:32][C:33]1[CH:38]=[CH:37][C:36](OS(C(F)(F)F)(=O)=O)=[CH:35][CH:34]=1)[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CCOC(C)=O>[CH3:20][O:21][C:22](=[O:47])[C@H:23]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=2[O:9][CH3:10])=[CH:37][CH:38]=1)[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26]

Participants

Conditions

Temperature: 80 °C

Procedure

2,6-Dimethoxybenzeneboronic acid (0.5 g) was dissolved in DME (10 mL). To the solution was added K2CO3 (0.7 g), N-(tert-butoxycarbonyl)-O-(trifluoromethane-sulfonyl)-L-tyrosine methyl ester (0.4 g), Pd(Ph3P)4 (0.6 g) and water (0.2 mL). The resulting mixture was heated to 80° C. overnight. Subsequently EtOAc and water were added to the mixture. The EtOAc layer was dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:2) to give N-(tert-butoxycarbonyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (380 mg).

Workup

dry with materialThe EtOAc layer was dried (MgSO4)
customevaporated
customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:2)

Sources & evidence

ORD record: ord-ed9c09b43732410cac601d6ce68c8ca5
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855843B2

Reaction notes

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