Diethyl Pyrocarbonate → HCID 14649921, compound

HRID 1165063Notes

Reaction equation

HRID 1165063 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([OH:20])=O)[CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2].[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOC(OC(OCC)=O)=O.C(N(CC)CC)C>CN(C=O)C.O>[CH2:26]([NH:33][C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:6]([OH:25])=[C:7]([C:21]([CH3:23])([CH3:22])[CH3:24])[CH:8]=1)=[O:20])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 7504BenzylamineHCID 8471TriethylamineHCID 13960405HCID 13960405, compound2×

Product 1

HCID 14649921HCID 14649921, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A 1 g quantity of 2,6-di-tert-butyl-4-(2-carboxyphenylamino)phenol (Compound 25) was dissolved in 20 ml of DMF. To the solution were added with ice-cooling 340 mg of benzylamine and 570 mg of DEPC and then added a solution of 330 mg of triethylamine in 5 ml of DMF over 20 minutes. Then the reaction mixture was stirred at room temperature for 20 hours, and then poured into water, and extracted with ethyl acetate. The organic layer was washed with water, dried over MgSO4 and concentrated to give a crude product which was purified by silica gel column chromatography (eluent: diethyl ether-hexane=1:10→1:5), giving 1.1 g of the title compound as white crystals.

Workup

  1. additionTo the solution were added with ice-
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a crude product which
  7. customwas purified by silica gel column chromatography (eluent: diethyl ether-hexane=1:10→1:5)

Sources & evidence

ORD record
ord-4140d7f5d59d43968f5a7e705c7a337e
Source dataset
uspto-grants-1990_03
Patent number
US04906662

Reaction notes

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