Potassium Carbonate → HCID 57563153, compound

HRID 1726200Notes

Reaction equation

HRID 1726200 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][CH:38]=1)[CH2:6][N:7]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:28])[CH2:15][CH2:16][NH:17][C:18](=[O:27])[C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])[CH2:10][CH2:9]1)#[N:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:46][C:47]([O:49][CH3:50])=[O:48]>CN(C=O)C>[CH3:50][O:49][C:47](=[O:48])[CH2:46][O:35][C:32]1[CH:33]=[CH:34][C:29]([N:7]([CH2:6][C:5]2[CH:36]=[CH:37][CH:38]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH:14]([CH3:28])[CH2:15][CH2:16][NH:17][C:18](=[O:27])[C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:26])[CH2:10][CH2:9]2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57563088HCID 57563088, compound

Product 1

HCID 57563153HCID 57563153, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of COMPOUND 117 (102 mg, 0.20 mmol) in DMF (1 mL) were added K2CO3 (86 mg, 0.62 mmol) followed by methyl bromoacetate (40 μL, 0.42 mmol) and the mixture was stirred at room temperature overnight to afford COMPOUND 147 as a tan solid (97 mg, 82%) following work-up and purification. 1H NMR (CDCl3) δ 0.90-1.13 (m, 2H), 0.99 (d, 3H, J=6.3 Hz), 1.49-1.54 (m, 1H), 1.69-1.81 (m, 3H), 2.12 (t, 1H, J=12.0 Hz), 2.31 (s, 6H), 2.53 (t, 1H, J=11.7 Hz), 2.73-2.88 (m, 3H), 3.24-3.31 (m, 1H), 3.41-3.49 (m, 1H), 3.71 (s, 2H), 3.78 (s, 3H), 3.86-3.90 (m, 1H), 4.52 (s, 2H), 6.51 (d, 2H, J=8.1 Hz), 6.73 (d, 2H, J=8.4 Hz), 6.94-7.00 (m, 3H), 7.42-7.50 (m, 4H), 8.42 (br s, 1H). 13C NMR (CDCl3) δ 13.79, 19.51, 29.43, 30.68, 31.28, 40.19, 44.01, 49.03, 52.51, 58.07, 60.86, 66.52, 112.73, 116.20, 116.37, 119.42, 127.62, 128.72, 129.51, 130.61, 130.78, 131.56, 134.42, 139.02, 142.79, 143.83, 150.85, 162.90, 170.14, 170.22. ES-MS m/z 583 (M+H). Anal. Calcd. for C35H422N4O4.0.3H2O: C, 71.48; H, 7.30; N, 9.53. Found. C, 71.42; H, 7.23; N, 9.40.

Sources & evidence

ORD record
ord-6844cda894a44f18add4e6056440aca1
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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