4-Methylmorpholine → HCID 57206008, compound

HRID 2269813Notes

Reaction equation

HRID 2269813 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:16][C:17](=[O:31])[CH:18]([NH2:30])[C:19]([NH:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:32][C@H:33]([CH:37]([CH3:39])[CH3:38])[C:34](O)=[O:35].CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>C(OCC)(=O)C.CCCCCC.ClCCl>[CH2:22]([NH:21][C:19](=[O:20])[CH:18]([NH:30][C:34](=[O:35])[C@H:33]([Br:32])[CH:37]([CH3:39])[CH3:38])[C:17]([NH:16][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:31])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 156968alpha-Bromoisovaleric acid, (R)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69989911HCID 69989911, compound

Product 1

HCID 57206008HCID 57206008, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine N,N′-diphenethyl-2-aminomalonamide trifluoroacetic acid salt (0.285 g, 0.655 mmol) and dichloromethane (5 mL). Add (R)-2-bromo-3-methylbutyric acid (0.118 g, 0.655 mmol), N-methylmorpholine (0.10 mL, 0.983 mmol), and 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (0.14 g, 0.725 mmol), and 1 -hydroxybenztriazole hydrate (0.10 g, 0.72 mmol). After 18 hours, evaporate the reaction mixture in vacuo, dilute the concentrated reaction mixture with ethyl acetate, extract with an aqueous 5% sulfuric acid solution, a saturated sodium bicarbonate solution, and then brine. Saturate each of the aqueous layers with sodium chloride and extract four times with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give the title compound (67%).

Workup

  1. customevaporate the reaction mixture in vacuo
  2. additiondilute
  3. customthe concentrated reaction mixture with ethyl acetate
  4. extractionextract with an aqueous 5% sulfuric acid solution
  5. concentrationSaturate each of the aqueous layers with sodium chloride
  6. extractionextract four times with ethyl acetate
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-0988dfecb41b40078a6e0d4c1333b18f
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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