Acetaminophen → HCID 18348668, compound

HRID 2268559Notes

Reaction equation

HRID 2268559 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:10][CH2:9][C:8]2[C:11](=[O:20])[C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[C:14](=[O:15])[C:7]=2[CH2:6][CH2:5]1.O[C:22]1[CH:31]=[CH:30][C:25]([NH:26][C:27](=[O:29])[CH3:28])=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:27]([NH:26][C:25]1[CH:30]=[CH:31][C:22]([O:1][CH2:2][CH2:3][CH:4]2[CH2:10][CH2:9][C:8]3[C:11](=[O:20])[C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[C:14](=[O:15])[C:7]=3[CH2:6][CH2:5]2)=[CH:23][CH:24]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 1983AcetaminophenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 183485737-(2-Hydroxyethyl)-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione

Product 1

HCID 18348668HCID 18348668, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-(2-hydroxyethyl)-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione (101 mg), p-hydroxyacetanilide (166 mg), and triphenylphosphine (126 mg) in THF (2 ml) was added a solution of diethyl azodicarboxylate (81 mg) in THF (1 ml) at room temperature. The reaction mixture was stirred at room temperature for 80 min and concentrated. The residue was purified successively by silica gel column chromatography (eluent:ethyl acetate/hexane=1/1) and by alumina column chromatography (eluent:ethyl acetate/hexane=1/1) and then with recrystallization from ethyl acetate-hexane to obtain the entitled compound (93 mg).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified successively by silica gel column chromatography (eluent:ethyl acetate/hexane=1/1) and by alumina column chromatography (eluent:ethyl acetate/hexane=1/1)
  3. customwith recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b584b7a69a1d47bb95f24a5eea626d99
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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