Dimethylformamide → HCID 68818602, compound

HRID 900355Notes

Reaction equation

HRID 900355 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]([C:19]3[CH:30]=[CH:29][C:22]([CH2:23]OS(C)(=O)=O)=[CH:21][CH:20]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:31][O:32][C:33](=[O:45])[C@H:34]([CH2:43][SH:44])[NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH3:31][O:32][C:33](=[O:45])[CH:34]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:40])[CH3:41])=[O:37])[CH2:43][S:44][CH2:23][C:22]1[CH:21]=[CH:20][C:19]([C:9]2[N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 10977409N-(tert-Butoxycarbonyl)-L-cysteine methyl esterHCID 59696192HCID 59696192, compound

Product 1

HCID 68818602HCID 68818602, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Methanesulfonic acid 4-(4,6-diphenylpyrimidin-2-yl)-benzyl ester, 0.15 g (0.36 mmol), N-(tert-Butoxycarbonyl)-L-cysteine methyl ester, 0.08 mL (0.36 mmol), cesium carbonate, 235 mg (0.72 mmol), and 10 mL of N,N-dimethylformamide was stirred at room temperature for 4 h. The mixture was diluted with 10 mL of water and extracted with 2×50 mL of ethyl acetate. The organic layer was washed with 2×50 mL portions of aq. LiCl, sat. aq. NaHCO3, sat. aq. NaCl, and dried (MgSO4). After the solution was concentrated, the residue was purified by column chromatography (eluted with 7% EtOAc-Heptane) to afford the desired product in 0.18 g (90%) as a white solid. 1H NMR (CDCl3) 8.67 (d, 2H, J=9.0 Hz), 8.30-8.27 (m, 4H), 8.02 (s, 1H), 7.61-7.55 (m, 6H), 7.47 (d, 2H, J=9.0 Hz), 5.30 (d, 1H, J=7.7 Hz), 4.63-4.52 (m, 1H), 3.82 (s, 2H), 3.76 (s, 3H), 2.93 (dd, 1H, J=15.7, 6.0 Hz), 2.84 (dd, 1H, J=15.7, 6.7 Hz), 1.47 (s, 9H).

Workup

  1. extractionextracted with 2×50 mL of ethyl acetate
  2. washThe organic layer was washed with 2×50 mL portions of aq. LiCl, sat. aq. NaHCO3, sat. aq. NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationAfter the solution was concentrated
  5. customthe residue was purified by column chromatography (eluted with 7% EtOAc-Heptane)

Sources & evidence

ORD record
ord-a4178c82cae642b3858b87e1f3998e55
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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