Dimethylformamide → HCID 68322429, compound
Reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])[CH3:3].CN(C)C=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][C:49]2[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=2)=[CH:44][C:43]=1[O:56][CH3:57]>>[CH3:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[C:11]([NH:53][C:52]1[CH:51]=[CH:50][C:49]([O:48][C:45]2[CH:46]=[CH:47][C:42]([CH3:41])=[C:43]([O:56][CH3:57])[CH:44]=2)=[CH:55][CH:54]=1)=[O:13]Participants
Procedure
To a solution of N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-alanine (182 mg, 0.960 mmol) in dry N,N-Dimethylformamide (DMF) (4 mL) DIPEA (0.305 mL, 1.745 mmol) and then TBTU (336 mg, 1.047 mmol) were added and the reaction mixture was stirred for 15 minutes at r.t. 4-{[4-methyl-3-(methyloxy)phenyl]oxy}aniline (Intermediate 20, 200 mg) was then added and the reaction mixture was stirred for 1 hour at the same temperature. The reaction was quenched with water (2 mL), diluted with brine (10 mL) and extracted with ethyl acetate (2 times 20 mL). Organic layer was dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system, 10 g SNAP column) using as eluent a gradient cyclohexane/ethyl acetate from 100/0 to 80/20 to afford the title compound as a yellow pale solid (304 mg).
Workup
- stirringthe reaction mixture was stirred for 1 hour at the same temperature
- customThe reaction was quenched with water (2 mL)
- additiondiluted with brine (10 mL)
- extractionextracted with ethyl acetate (2 times 20 mL)
- dry with materialOrganic layer was dried over sodium sulphate
- filtrationfiltered
- customevaporated
- customthe residue was purified by flash chromatography (Biotage system, 10 g SNAP column)
Sources & evidence
- ORD record
- ord-3bcea0eaf6d54d919071ffb8fc780287
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216967B2
Reaction notes
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