Dimethylformamide → HCID 86600979, compound

HRID 1241473Notes

Reaction equation

HRID 1241473 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:12]([C@@H:23]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH3:24])[C:13](=[O:22])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.[CH:32]1[CH:37]=[CH:36][C:35]([Se:38]Br)=[CH:34][CH:33]=1.CN(C)C=O>C(#N)C.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[N:12]([C@@H:23]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)[CH3:24])[C:13](=[O:22])[CH:14]([Se:38][C:35]3[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=3)[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:11][C:9]2=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 123446BromoselenobenzeneHCID 69630388HCID 69630388, compound

Product 1

HCID 86600979HCID 86600979, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6342AcetonitrileSolvent

Procedure

Silver triflate (1.69 g, 6.6 mmol) was added to a stirred solution of (S)-α-(4-chlorophenyl)-α-[(R)-N-[1-(4-chlorophenyl)ethyl]-N-(cinnamoyl)amino]acetamide (1.5 g, 3.3 mmol), in acetonitrile (120 mL). To the resulting solution was successively added benzeneselenyl bromide (1.54 g, 6.53 mmol) and dimethylformamide (5.2 mL). After 6 h, the solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate (100 mL) and 1N sodium hydrogenocarbonate (70 mL), dried (Na2SO4), and evaporated. Purification by column chromatography (AcOEt/hexanes, 1:3) afforded the title compound, which was recrystallized from Et2O to give colorless prisms (855 mg, 43%): 1H NMR (400 MHz, CDCl3) δ 1.68 (d, J=7.0 Hz, 3H, CH3), 4.29 (d, J=12.2 Hz, 1H, CH), 4.79 (d, J=12.2 Hz, 1H, CH), 5.28 (s, 1H, CH), 6.21–6.25 (m, 3H, ArH), 6.31 (q, J=7.0 Hz, 1H, CH), 6.71–6.76 (m, 4H, ArH), 6.93–7.11 (m, 6H, NH+5ArH), 7.34–7.40 (m, 4H, ArH), 7.50 (d, J=8.4 Hz, 2H, ArH). Mass spectrum (LCMS, ESI pos.): Calcd for C31H26Cl2N2O2Se: 608.0; found: 609.0 (M+H)+.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate (100 mL) and 1N sodium hydrogenocarbonate (70 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customPurification by column chromatography (AcOEt/hexanes, 1:3)

Sources & evidence

ORD record
ord-36e0304adf694d579530e2a214518871
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

Loading…