Beta-Alanine → HCID 135854487, compound

HRID 1351451Notes

Reaction equation

HRID 1351451 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])[CH:7]=O)([CH3:3])[CH3:2].[C:16]1([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[S:30])[CH2:27][C:28]#[N:29])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.NCCC(O)=O>C(O)C>[CH:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[C:27](/[C:26]([NH:25][CH2:24][CH2:23][CH2:22][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[S:30])\[C:28]#[N:29])[CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeHCID 54079284HCID 54079284, compound

Product 1

HCID 135854487HCID 135854487, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.6 g of 3,5-diisopropyl-4-hydroxybenzaldehyde, and 0.6 g of N-3-phenyl-n-propylcyanothioacetamide and 40 mg β-alanine in 40 ml ethanol were refluxed 4 hours. Evaporation and chromatography gave 0.6 g of M24 as an orange viscous oil that did not crystalyze. NMR CDCl3 δ 8.76(1H, S, vinyl), 7.78(2H, S, H2.6), 7.25(5H, m), 5.60(1H, S, OH), 3.90(2H, q, J=7.0 Hz), 3.17(2H, Septet, J=7.0 Hz), 2.76(2H, t, J=7.0 Hz), 2.11(2H, quintet, J=7.0 Hz), 1.29(12H, d, J=7.0 Hz). MS—407(M+1,55), 406(M+, 70), 373(M-CH3-H2O, 100), 363(M-isopropyl, 72), 272(M-NH(CH2)3 Ph. 20), 259 (58), 230 (28), 91 (28), m/e.

Workup

  1. customEvaporation and chromatography
  2. customgave 0.6 g of M24 as an orange viscous oil that

Sources & evidence

ORD record
ord-22ef765113e54ca78a8b0edd7e56630b
Source dataset
uspto-grants-2007_05
Patent number
US07217737B2

Reaction notes

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