4-Methylmorpholine → HCID 71087476, compound

HRID 927366Notes

Reaction equation

HRID 927366 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[NH:49]([CH:51]=[O:52])[NH2:50]>CN(C=O)C>[CH:51]([NH:49][NH:50][C:13](=[O:15])[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:17])[CH3:16])=[O:52]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 12229HydrazinecarboxaldehydeHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71087476HCID 71087476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(benzyloxycarbonylamino)-2-methylpropanoic acid (Example 8 a, 1.9 g, 8 mmol), HATU (CAN 148893-10-1, 3.97 g, 10 mmol) and N-methylmorpholine (CAN 109-02-4, 2.43 g, 24 mmol) in DMF (20 mL) was stirred at room temperature for 15 min. Then hydrazinecarboxaldehyde (CAN 624-84-0, 0.53 g, 9 mmol) was added and the reaction mixture was stirred at room temperature overnight. After evaporation of solvents, the residue was diluted with ethyl acetate (30 mL) and water (30 mL). The organic layer was washed with saturated sodium bicarbonate solution (30 mL), hydrochloric acid (30 mL, 1 M), brine (30 mL) and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure left the title compounds as yellow oil (2.1 g, 94%); MS: m/e 280.1 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customAfter evaporation of solvents
  3. additionthe residue was diluted with ethyl acetate (30 mL) and water (30 mL)
  4. washThe organic layer was washed with saturated sodium bicarbonate solution (30 mL), hydrochloric acid (30 mL, 1 M), brine (30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the solvent under reduced pressure
  7. waitleft the title compounds as yellow oil (2.1 g, 94%)

Sources & evidence

ORD record
ord-118917c07a7b4ffbae253eabc39dd6d4
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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