Hydrochloric Acid → HCID 67623405, compound

HRID 1940391Notes

Reaction equation

HRID 1940391 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[S:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]([NH:19][CH2:20][C:21]([C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[C:25]([O:34][CH2:35]C2C=CC=CC=2)[CH:24]=1)=[O:22])=[O:18].[CH2:42]([N:44](CC)CC)[CH3:43].C(N=C=[O:53])C.Cl>CN(C=O)C.O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[S:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]([NH:19][CH2:20][C:21]([C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[C:25]([O:34][C:35](=[O:53])[NH:44][CH2:42][CH3:43])[CH:24]=1)=[O:22])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 67622880HCID 67622880, compound

Product 1

HCID 67623405HCID 67623405, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the solution of the compound prepared in Example 50 (a) (280 mg, 0.512 mmole) in DMF were added triethylamine (0.1 ml) and ethyl isocyanate (50 μl), and the mixture was stirred at room temperature for 4 hours. To the reaction solution was added water, and the mixture was acidified with 1N hydrochloric acid. The solution was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After the inorganic salt was removed by filtration, the filtrate was concentrated under reduced pressure. The oily product thus obtained was purified by column chromatography on silica gel with an eluent system of chloroform:methanol=100:1 to give 175 mg of the title compound as a pale yellow foam product (yield, 55%).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter the inorganic salt was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe oily product thus obtained
  6. customwas purified by column chromatography on silica gel with an eluent system of chloroform
  7. custommethanol=100:1 to give

Sources & evidence

ORD record
ord-92236138e5e44addae10f07a88d34db5
Source dataset
uspto-grants-1997_12
Patent number
US05698692

Reaction notes

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