Triethylamine → HCID 67165236, compound

HRID 552379Notes

Reaction equation

HRID 552379 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[NH:7][C:8](=[O:14])[NH:9]2)[CH:2]=[CH2:3].C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C=O)C.O>[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[N:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:8](=[O:14])[NH:9]2)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19604250HCID 19604250, compound

Product 1

HCID 67165236HCID 67165236, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of Step 4 intermediate (1.28 g, 6.33 mmol) in dry DMF (6.3 ml) was added triethylamine (4.38 ml, 31.35 mmol) and ethyl chloroformate (3.03 ml, 31.65 mmol). The reaction was stirred at room temperature for 24 h. The reaction was diluted with water, extracted with ethyl acetate, washed with brine and dried over Na2SO4. Purification of the crude product by silica gel column chromatography using 1% ethyl acetate in chloroform afforded 1.3 g of the title compound; 1H NMR (δ ppm, CDCl3, 300 MHz): 9.56 (br.s, 1H); 7.49 (t, J=7.8, 1H); 7.05 (d, J=7.2, 1H); 6.93 (d, J=8.4, 1H); 6.11-5.90 (m, 1H), 5.07-4.98 (m, 2H); 4.53 (q, J=7.2, 2H); 3.96 (d, J=6.3, 2H); 1.46 (t, J=7.2, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customPurification of the crude product by silica gel column chromatography

Sources & evidence

ORD record
ord-37e4b51b09174996b57ed073e378837a
Source dataset
uspto-grants-2011_05
Patent number
US07951814B2

Reaction notes

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