Trifluoroacetic acid → (2R)-2-amino-N-{6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinyl}butanamide

HRID 527584Notes

Reaction equation

C(O)(C(F)(F)F)=O.[CH2:8]([CH:10]1[C:14]2[C:15]([O:19][C:20]3[N:25]=[CH:24][C:23]([NH:26][C:27]([C@H:29]([NH:32]C(=O)OC(C)(C)C)[CH2:30][CH3:31])=[O:28])=[CH:22][CH:21]=3)=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][O:11]1)[CH3:9]>ClCCl>[NH2:32][C@H:29]([CH2:30][CH3:31])[C:27]([NH:26][C:23]1[CH:24]=[N:25][C:20]([O:19][C:15]2[C:14]3[CH:10]([CH2:8][CH3:9])[O:11][CH2:12][C:13]=3[CH:18]=[CH:17][CH:16]=2)=[CH:21][CH:22]=1)=[O:28]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 50 ml round-bottomed flask 1,1-dimethylethyl {(1R)-1-[({6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinyl}amino)carbonyl]propyl}carbamate (Intermediate 109, 12.7 mg) was dissolved in dichloromethane (3 ml) to give a colourless solution. The reaction mixture was cooled at 0° C. TFA (1.5 ml, 19.47 mmol) was added at that temperature. The reaction mixture was stirred at 0° C. After 1 hour, the reaction was completed. The reaction mixture was evaporated under vacuum affording the crude product which was charged on a 2 g SCX cartridge. It was then flushed with 15 ml of MeOH followed by 15 ml of a solution of ammonia in MeOH (2M). The ammonia eluate was evaporated under vacuum to afford the title compound as a colorless oil (9.0 mg).

Workup

customto give a colourless solution
customThe reaction mixture was evaporated under vacuum
customaffording the crude product which
additionwas charged on a 2 g SCX cartridge
customIt was then flushed with 15 ml of MeOH
customThe ammonia eluate was evaporated under vacuum

Sources & evidence

ORD record: ord-9e6bb5fc0e114fc89e90b9d544e688e8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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