Diisopropylethylamine → HCID 58696281, compound

HRID 1178330Notes

Reaction equation

HRID 1178330 reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7]([C:9]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)([CH2:13][NH:14][CH3:15])[CH2:10][CH:11]=[CH2:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]([F:32])([F:31])[CH2:27][C:28](O)=[O:29].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[C:1]([O:5][C:6](=[O:24])[N:7]([C:9]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)([CH2:13][N:14]([CH3:15])[C:28](=[O:29])[CH2:27][C:26]([F:32])([F:31])[F:25])[CH2:10][CH:11]=[CH2:12])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 27779723,3,3-Trifluoropropionic acid2×HCID 27960291-Hydroxybenzotriazole hydrate2×HCID 58696296HCID 58696296, compound

Product 1

HCID 58696281HCID 58696281, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

tert-Butyl[1-(3,4-dichlorophenyl)-1-methylaminomethyl-3-butenyl]methylcarbamate (5.0 g) was dissolved in N,N-dimethylformamide (50 mL), and, at room temperature, 3,3,3-trifluoropropionic acid (1.3 mL), [2-(1H)-benzotriazole-1-yl]-1,1,3,3-tetramethyluronium hexafluorophosphate (5.6 g), 1-hydroxybenzotriazole monohydrate (2.0 g), and N,N-diisopropylethylamine (3.5 mL) were added thereto, followed by stirring for 2 hours at room temperature. 3,3,3-Trifluoropropionic acid (0.6 mL), [2-(1H)-benzotriazole-1-yl]-1,1,3,3-tetramethyluronium hexafluorophosphate (2.5 g), 1-hydroxybenzotriazole monohydrate (1.0 g), and N,N-diisopropylethylamine (1.75 mL) were added to the reaction mixture, and the resultant mixture was stirred for 1 hour at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby give the title compound (3.38 g, 52%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over sodium sulfate anhydrate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f05ad7e983b94b0f9ce7ccb5ce256583
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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