Potassium Carbonate → HCID 54188732, compound

HRID 1060431Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[C:4]=1B(O)O)#[N:2].C([O-])([O-])=O.[K+].[K+].[CH3:20][O:21][C:22](=[O:50])[C@H:23]([CH2:35][C:36]1[CH:41]=[CH:40][C:39](OS(C(F)(F)F)(=O)=O)=[CH:38][CH:37]=1)[NH:24][C:25](=[O:34])[C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33]>C1(C)C=CC=CC=1.CCOC(C)=O.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>[CH3:20][O:21][C:22](=[O:50])[C@H:23]([CH2:35][C:36]1[CH:37]=[CH:38][C:39]([C:4]2[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][C:5]=2[C:9]#[N:10])=[CH:40][CH:41]=1)[NH:24][C:25](=[O:34])[C:26]1[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=1[Cl:32]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 2,6-dicyanobenzene boronic acid (0.516 g) and anhydrous K2CO3 (0.2 g) in toluene (10 mL) under N2 was added N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester (0.5 g). Pd(PPh3)4 (0.1 g) was added and the mixture was heated at 90° C. for 8 h. The mixture was cooled, diluted with EtOAc and washed successively with water and brine. The organic layer was dried (MgSO4) and evaporated, and the residue was purified by column chromatography (silica gel; eluent: EtOAc/hexane 1/1) to yield 58 mg of N-(2,6-dichlorobenzoyl)-4-(2,6-dicyanophenyl)-L-phenylalanine methyl ester.

Workup

temperatureThe mixture was cooled
washwashed successively with water and brine
dry with materialThe organic layer was dried (MgSO4)
customevaporated
customthe residue was purified by column chromatography (silica gel; eluent: EtOAc/hexane 1/1)

Sources & evidence

ORD record: ord-570c32343a01497fbb753d85c2833647
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521666B1

Reaction notes

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