Diisopropylethylamine → Benzamide

HRID 1621180

Reaction equation

F[C:2]1[C:14](F)=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6]CC(O)=O)=[O:5].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC(C)C[C@@H](B1O[C@@H]2C[C@@H]3C[C@H]([C@]2(C)O1)C3(C)C)N.FC(F)(F)C([O-])=O.CCN(C(C)C)C(C)C>CN(C)C=O>[C:4]([NH2:6])(=[O:5])[C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [(2,3-difluorobenzoyl)amino]acetic acid (0.205 g, 0.95 mmol) in dimethylformamide (10 mL) were added TBTU (0.337 g, 1.0 mmol) and (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butan-1-amine as its trifluoroacetate salt (0.362 g, 0.95 mmol). The mixture was allowed to cool to 0° C. and DIEA (0.498 mL, 2.9 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water (100 mL) and the product partitioned into DCM. The organic layer was dried over sodium sulfate and the solvent removed to give 2,3-difluoro-N-[2-({1R)-3-methyl-1-[(3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide.

Workup

temperatureto warm to room temperature
customThe reaction was quenched with water (100 mL)
customthe product partitioned into DCM
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent removed

Sources & evidence

ORD record: ord-474a7b3a6cae4cc7a2fc1d8e651e0575
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772536B2

Linked notes

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