Ethanol → HCID 89545399, compound

HRID 873340Notes

Reaction equation

CN(C)[CH2:3][CH2:4]CN=C=NCC.C(O)C.[C:15]([CH:17]([C:30]1[CH:31]=[N:32][CH:33]=[C:34]([Br:36])[CH:35]=1)[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH2:19][C:20]([OH:22])=[O:21])#[N:16]>CN(C)C1C=CN=CC=1.ClCCl>[C:15]([CH:17]([C:30]1[CH:31]=[N:32][CH:33]=[C:34]([Br:36])[CH:35]=1)[CH:18]([C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1)[CH2:19][C:20]([O:22][CH2:3][CH3:4])=[O:21])#[N:16]

Participants

Conditions

Temperature: 25 °C

Procedure

Under protective gas (Ar), 0.121 g (0.632 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDC), a spatula tip of 4-dimethylaminopyridine (DMAP) and 0.061 g (1.317 mmol) of ethanol were added to 0.200 g (0.527 mmol) of 4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoic acid (Example A4) in 4 ml of dichloromethane, and the mixture was stirred at 25° C. for 8 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane and washed twice with in each case 15 ml of water. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (gradient: starting with ethyl acetate/heptane=5:95 over the course of 20 minutes increased to ethyl acetate/heptane=20:80) gave 0.143 g (67% of theory) of the title compound (erythro:threo=58:42). 1H-NMR in CDCl3 see Table 2.

Workup

customThe solvent was removed under reduced pressure
washwashed twice with in each case 15 ml of water
dry with materialThe combined organic phases were dried over sodium sulphate
customthe solvent was removed under reduced pressure
customstarting with ethyl acetate/heptane=5:95 over the course of 20 minutes
temperatureincreased to ethyl acetate/heptane=20:80)

Sources & evidence

ORD record: ord-9603731a85af45138783b2d3f817d09e
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975412B2

Reaction notes

Loading…