4-Methylmorpholine → HCID 86757672, compound

HRID 2269819Notes

Reaction equation

HRID 2269819 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.[C:32]([C@H:35]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:36](O)=[O:37])(=[S:34])[CH3:33].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:36](=[O:37])[C@@H:35]([C:32](=[S:34])[CH3:33])[CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[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 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69989911HCID 69989911, compoundHCID 86757673HCID 86757673, compound

Product 1

HCID 86757672HCID 86757672, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine N,N′-diphenethyl-2-aminomalonamide trifluoroacetic acid salt (0.50 g, 1.0 mmol) and dichloromethane (15 mL). Add (R)-2-thioacetyl-4-phenylbutyric acid (0.545 g, 1.0 mmol), N-methylmorpholine (0.22 mL, 2.0 mmol), and 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (0.23 g, 1.2 mmol), and 1-hydroxybenztriazole hydrate (0.16 g, 1.2 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. Extract each aqueous layer 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 3/2 ethyl acetate/hexane to give the title compound (92%).

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. extractionExtract each aqueous layer with ethyl acetate
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue

Sources & evidence

ORD record
ord-1283e0c9c4ad4f339957068f24550f63
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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