Triethylamine → benzyl (3R)-3-(4-cyanobenzoylamino)-4-(3-cyanophenoxy)butanoate

HRID 747705Notes

Reaction equation

C(O[C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])(C)(C)C.[C:31]([C:33]1[CH:41]=[CH:40][C:36](C(Cl)=O)=[CH:35][CH:34]=1)#[N:32].C(N(CC)CC)C.C(OCC)(=O)C>Cl.O1CCOCC1>[C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[O:7])=[CH:35][CH:34]=1)#[N:32]

Participants

Conditions

Temperature: 0 °C

Procedure

1.8 g (4.38 mmol) of benzyl (3R)-3-t-butoxycarbonylamino-4-(3-cyanophenoxy)butyrate was dissolved in 20 ml of 4 N solution of hydrogen chloride in dioxane, and the solution was stirred at 0° C. for 6 hours. The solvent was evaporated, and the oily residue was dissolved in 5 ml of dichloromethane. 1.09 g (6.58 mmol) of 4-cyanobenzoyl chloride and 1.22 ml (8.76 mmol) of triethylamine were added to the solution under cooling with ice, and they were stirred at room temperature overnight. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

customThe solvent was evaporated
dissolutionthe oily residue was dissolved in 5 ml of dichloromethane
temperatureunder cooling with ice, and they
stirringwere stirred at room temperature overnight
customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-d7ecd08be8d841e3ae21f99f7fd3381e
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396844B1

Reaction notes

Loading…