Triethylamine → HCID 86656350, compound

HRID 1942466Notes

Reaction equation

HRID 1942466 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([C:15]([N:17]([CH:31]([CH3:33])[CH3:32])[C@@H:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)=[O:16])[C:12]([CH3:14])=[CH:13][C:8]=2[O:7][C:6]([CH3:35])([CH3:34])[C:5]1=[O:36].ClC(Cl)(O[C:41](=[O:47])OC(Cl)(Cl)Cl)Cl.[CH2:49]([N:51](CC)CC)C>C(Cl)(Cl)Cl>[CH:31]([N:17]([C:15]([C:11]1[C:12]([CH3:14])=[CH:13][C:8]2[O:7][C:6]([CH3:34])([CH3:35])[C:5](=[O:36])[N:4]([CH2:3][CH2:2][NH:1][C:41]([NH:51][CH3:49])=[O:47])[C:9]=2[CH:10]=1)=[O:16])[C@@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:19]1)([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67331189HCID 67331189, compound

Product 1

HCID 86656350HCID 86656350, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To tert-butyl (3R)-3-[{[4-(2-aminoethyl)-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (200 mg) were added triphosgene (47 mg), triethylamine (0.12 ml) and chloroform (5 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, the reaction solution was concentrated, and thereto were added methylamine (0.17 ml) and chloroform (5 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. The obtained ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform /methanol=9/1) to give the title compound (70 mg) as colorless amorphous.

Workup

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated
  3. additionwere added methylamine (0.17 ml) and chloroform (5 ml) under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature for 2 hours
  6. additionwater was added to the reaction solution
  7. extractionthe mixture was extracted with ethyl acetate solution
  8. washThe obtained ethyl acetate solution was washed with water
  9. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe obtained residue was purified by silica gel column chromatography (chloroform /methanol=9/1)

Sources & evidence

ORD record
ord-4f5efb4fe1504818bfca295e82fc86e7
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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