Potassium Carbonate → HCID 56594793, compound

HRID 527190Notes

Reaction equation

HRID 527190 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[C:27](=[O:28])[NH:26][N:25]=[CH:24]4)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C[C:30]1[CH:35]=[CH:34][C:33](S(OCCC#CCC)(=O)=O)=[CH:32][CH:31]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>>[CH2:34]([N:26]1[C:27](=[O:28])[N:23]([C:20]2[CH:21]=[CH:22][C:17]([N:14]3[CH2:13][CH2:12][N:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=4)[CH2:16][CH2:15]3)=[CH:18][CH:19]=2)[CH:24]=[N:25]1)[CH2:35][C:30]#[C:31][CH2:32][CH3:33]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 14967550HCID 14967550, compoundHCID 56593708HCID 56593708, compound

Product 1

HCID 56594793HCID 56594793, compoundYield 60%

Procedure

This compound was synthesized as a yellowish amorphous solid from 13 (56.0 mg, 0.147 mmol), 3o (48.2 mg, 0.191 mmol), K2CO3 (40.6 mg, 0.294 mmol), and 18-Crown-6 (38.9 mg, 0.147 mmol) in 60% yield by following general procedure 1.3: 1H NMR (400 MHz, CDCl3, δH) 7.61 (s, 1H), 7.45-7.34 (m, 2H), 7.10-6.87 (m, 6H), 5.12 (s, 2H), 3.97 (t, J=7.3 Hz, 2H), 3.47 (s, 3H), 3.35 (dd, J=6.3, 3.6 Hz, 4H), 3.23 (dd, J=6.3, 3.6 Hz, 4H), 2.63 (tt, J=7.3, 2.3 Hz, 2H), 2.14 (qt, J=7.5, 2.3 Hz, 2H), 1.09 (t, J=7.5 Hz, 3H); 13C NMR (100 MHz, CDCl3, δC) 152.25, 151.76, 150.85, 146.67, 134.50, 125.93, 123.81, 118.52, 117.50, 116.85, 95.28, 83.95, 75.42, 56.10, 50.72, 49.39, 45.03, 19.25, 14.34, 12.62. MALDI-MS: 462.2 (M+H+), 484.2 (M+Na+).

Sources & evidence

ORD record
ord-634a101683de4863a2afca1cc48812b2
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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