Diisopropylethylamine → HCID 86678898, compound

HRID 1620738Notes

Reaction equation

HRID 1620738 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C:10]([OH:13])([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH3:19][NH:20][CH3:21].C(N(C(C)C)C(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>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:20]([CH3:21])[CH3:19])=[O:16])[C:10]([OH:13])([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11075314N-(tert-Butoxycarbonyl)-3-hydroxy-L-valineHCID 22497844Dimethylamine methanol

Product 1

HCID 86678898HCID 86678898, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-3-hydroxy-L-valine (1.00 g), 2M dimethylamine methanol solution (2.14 mL) and N-ethyl-N-(1-methylethyl)propan-2-amine (1.11 g) in DMF (10 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.63 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 magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (670 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 magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-52438ffc569947baac61ac03ae46a1f4
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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