Dimethylamine → HCID 71247139, compound

HRID 1620690Notes

Reaction equation

HRID 1620690 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]([O:11][C:12]([NH:14][C@H:15]([C:20]([OH:22])=O)[CH2:16][C:17](O)=[O:18])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:23]([N:25](C(C)C)[CH:26](C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C.O>[CH2:4]([O:11][C:12](=[O:13])[NH:14][C@@H:15]([CH2:16][C:17]([N:25]([CH3:26])[CH3:23])=[O:18])[C:20]([N:2]([CH3:3])[CH3:1])=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2723942N-(Benzyloxycarbonyl)aspartic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71247139HCID 71247139, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 50% aqueous dimethylamine solution (2.16 g) and N-[(benzyloxy)carbonyl]-L-aspartic acid (2.13 g) and N-ethyl-N-(1-methylethyl)propan-2-amine (4.12 g) in DMF (20 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (6.06 g) at room temperature. The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (550 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-70b330f016d8497eb82835c60de45637
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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