Triethylamine → HCID 54721547, compound

HRID 481921Notes

Reaction equation

HRID 481921 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:5][C:4](=[O:14])[CH:3]=1.[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[S:25]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:17])[CH3:16].C(N(CC)CC)C>C(O)C>[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:5][C:4](=[O:14])[C:3]=1[S:25][C:19]1[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=1[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53941198HCID 53941198, compoundHCID 54686255HCID 54686255, compound

Product 1

HCID 54721547HCID 54721547, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared as described in General Method III using 95.6 mg of 5,6-dihydro-4-hydroxy-6-phenyl-2(1H)-pyridinone, 180 mg of toluene-4-thiosulfonic acid S-(2-isopropyl-5-methylphenyl) ester (prepared as per Ranasinghe and Fuchs, Synthetic Communications 18: 227, (1988)) and 0.08 ml of triethylamine in 5 ml of absolute ethanol. The solution was stirred overnight at room temperature. Purification by flash chromatography using CH2Cl2 /isopropanol (99/1 to 95/5) as eluent gave a solid (m.p. 184°-186° C.). 1H NMR (CDCl3) δ1.28 (d, 3H), 1.29 (d, 3H), 2.23 (s, 3H), 2.98 (d, 2H), 3.52 (qn, 1H), 4.85 (t, 1H), 5.63 (s, 1H), 6.78 (s, 1H), 6.96 (m, 1H), 7.14 (d, 1H), 7.35-7.44 (m, 5H), 7.55 (s, 1H).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-b01d7a2541724ecda1a62cb8aba68530
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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