Potassium Carbonate → HCID 57563078, compound

HRID 1726201Notes

Reaction equation

HRID 1726201 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[CH2:6][N:7]([CH:18]1[CH2:23][CH2:22][N:21]([CH:24]([CH3:38])[CH2:25][CH2:26][NH:27][C:28]([C:30]2[C:31]([CH3:37])=[N:32][CH:33]=[N:34][C:35]=2[CH3:36])=[O:29])[CH2:20][CH2:19]1)[C:8]1[CH:13]=[CH:12][C:11]([O:14]C(=O)C)=[CH:10][CH:9]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:49][C:50]([O:52][CH3:53])=[O:51]>CN(C=O)C>[CH3:53][O:52][C:50](=[O:51])[CH2:49][O:14][C:11]1[CH:10]=[CH:9][C:8]([N:7]([CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:18]2[CH2:23][CH2:22][N:21]([CH:24]([CH3:38])[CH2:25][CH2:26][NH:27][C:28]([C:30]3[C:31]([CH3:37])=[N:32][CH:33]=[N:34][C:35]=3[CH3:36])=[O:29])[CH2:20][CH2:19]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57563064HCID 57563064, compound

Product 1

HCID 57563078HCID 57563078, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of COMPOUND 138 (105 mg, 0.205 mmol) in DMF (1 mL) were added K2CO3 (87 mg, 0.63 mmol) followed by methyl bromoacetate (40 μL, 0.42 mmol) and the mixture was stirred at room temperature overnight to afford COMPOUND 148 as a tan solid (81 mg, 66%) following work-up and purification. 1H NMR (CDCl3) δ 0.86-1.03 (m, 5H), 1.52-1.60 (m, 1H), 1.74-1.78 (m, 3H), 2.14 (t, 1H, J=11.4 Hz), 2.51 (s, 6H), 2.51-2.59 (m, 1H), 2.72-2.88 (m, 3H), 3.29-3.48 (m, 2H), 3.78-3.83 (m, 6H), 4.53 (s, 2H), 6.53 (d, 2H, J=8.4 Hz), 6.75 (d, 2H, J=8.1 Hz), 7.40-7.44 (m, 1H), 7.49-7.54 (m, 3H), 8.71 (br s, 1H), 8.84 (s, 1H). 13C NMR (CDCl3) δ 11.37, 19.90, 27.17, 28.32, 28.69, 37.93, 41.60, 46.92, 49.93, 50.15, 55.37, 58.15, 64.12, 110.38, 113.84, 114.32, 116.98, 127.17, 128.17, 128.50, 128.83, 129.20, 139.97, 141.27, 148.72, 155.46, 161.02, 164.27, 167.71. ES-MS m/z 585 (M+H). Anal. Calcd. for C33H40N6O4.0.7H2O: C, 66.36; H, 6.99; N, 14.07. Found. C, 66.32; H, 6.83; N, 13.71.

Sources & evidence

ORD record
ord-94868456935d4ac8beedaf706124ce8b
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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