Triethylamine → HCID 54063423, compound

HRID 1979490Notes

Reaction equation

HRID 1979490 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].ClC(Cl)(O[C:19](=[O:25])OC(Cl)(Cl)Cl)Cl.C([N:29](CC)CC)C.[O:34]=[C:35]1[NH:41][C:40]2[CH:42]=[C:43]([CH3:46])[CH:44]=[CH:45][C:39]=2[N:38]([CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH2:37][C@H:36]1[NH2:53]>O1CCCC1.C(OCC)(=O)C.O>[O:34]=[C:35]1[NH:41][C:40]2[CH:42]=[C:43]([CH3:46])[CH:44]=[CH:45][C:39]=2[N:38]([CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH2:37][C@H:36]1[NH:53][C:19]([NH:29][C:14]1[CH:13]=[CH:12][C:4]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[CH:3][CH:2]=1)=[O:25]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2737408tert-Butyl-3-aminobenzoateHCID 54123612HCID 54123612, compound

Product 1

HCID 54063423HCID 54063423, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
6.5 °C

Procedure

Tert-butyl 3-aminobenzoate (1.63 g) was dissolved in tetrahydrofuran (30 ml), the solution was cooled to internal temperature 5-8° C. Triphosgene (0.91 g) was added to the solution, stirred for 5 minutes. Subsequently triethylamine (4.30 ml) was added thereto four times after divided into four portions. After the mixture was stirred at room temperature for 10 minutes, a solution of (R)-2-oxo-3-amino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (2.10 g) in tetrahydrofuran (10 ml) was added, the resultant mixture was stirred for one hour. Water and ethyl acetate were added the reaction mixture, and extracted. The organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, to thereby obtain 3.28 g of the title compound as amorphous (Yield: 86.8%).

Workup

  1. stirringAfter the mixture was stirred at room temperature for 10 minutes
  2. extractionextracted
  3. washThe organic layer was successively washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ca2df5decacf4ff89bed84f61a3bfc95
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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