4-Methylmorpholine → HCID 71087476, compound

HRID 631980Notes

Reaction equation

HRID 631980 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-1e90fa7ec5f84da2bcc37f5cc2f5a7e7
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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