(S)-tert-Butyl 1-cyano-2-(4'-cyano-3'-fluorobiphenyl-4-yl)ethylcarbamate → (S)-4'-(2-Amino-2-cyanoethyl)-3-fluorobiphenyl-4-carbonitrile

HRID 600297Notes

Reaction equation

[C:1]([C@@H:3]([NH:20]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([F:19])[CH:12]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[NH2:20][C@H:3]([C:1]#[N:2])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([F:19])[CH:12]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-tert-Butyl 1-cyano-2-(4′-cyano-3′-fluorobiphenyl-4-yl)ethylcarbamate (0.580 g) was stirred in formic acid (8 mL) and heated at 50° C. for 10 min. The cooled mixture was evaporated, dissolved in methanol and applied to a 10 g SCX column. The column was washed with methanol then eluted with 10% ammonia in methanol. The eluate was evaporated to give a solid (0.335 g).

Workup

customThe cooled mixture was evaporated
dissolutiondissolved in methanol
washThe column was washed with methanol
washthen eluted with 10% ammonia in methanol
customThe eluate was evaporated

Sources & evidence

ORD record: ord-96f34f6561434d4d952771a5773e00e5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902181B2

Reaction notes

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