Triethylamine → HCID 54721547, compound

HRID 357894Notes

Reaction equation

HRID 357894 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) δ 1.28 (d, 3 H), 1.29 (d, 3 H), 2.23 (s, 3 H), 2.98 (d, 2 H), 3.52 (qn, 1 H), 4.85 (t, 1 H), 5.63 (s, 1 H), 6.78 (s, 1 H), 6.96 (m, 1 H), 7.14 (d, 1 H), 7.35-7.44 (m, 5 H), 7.55 (s, 1 H).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-1309752c700a49838f7c606b7bb3f179
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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