Triethylamine → HCID 21201974, compound

HRID 1979302Notes

Reaction equation

HRID 1979302 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]([C:36]([CH2:38][N:39]1[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[N:43]([C:50](=[O:55])[C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:42][CH:41]([NH2:56])[C:40]1=[O:57])=[O:37])([CH3:35])([CH3:34])[CH3:33]>O1CCCC1>[C:32]([C:36]([CH2:38][N:39]1[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[N:43]([C:50](=[O:55])[C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:42][CH:41]([NH:56][C:14]([NH:1][C:2]2[CH:12]=[CH:11][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=2)=[O:16])[C:40]1=[O:57])=[O:37])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 21201993HCID 21201993, compound

Product 1

HCID 21201974HCID 21201974, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 3-aminobenzoate (340 mg) was dissolved in anhydrous tetrahydrofuran (50 ml), triphosgene (228 mg) was added, triethylamine (0.9 ml) was added thereto five times after divided into five portions over 15 minutes at 0° C., and the mixture was stirred at room temperature for 5 minutes. To this solution was added a solution of 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine that obtained from Step 2 in tetrahydrofuran (10 ml), the resultant mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 870 mg of the titled compound (Yield: 79%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-579bffdd5d5e437a97e8e9b6cb56ecd4
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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