4-Methylmorpholine → HCID 57135847, compound

HRID 2269822Notes

Reaction equation

HRID 2269822 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:15][C:16](=[O:29])[CH:17]([NH2:28])[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:30][C@H:31]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:32](O)=[O:33].CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>ClCCl.C(OCC)(=O)C.CCCCCC>[CH2:21]([NH:20][C:18](=[O:19])[CH:17]([NH:28][C:32](=[O:33])[C@H:31]([Br:30])[CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:16]([NH:15][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:29])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11746403(R)-2-Bromo-3-phenylpropionic acidHCID 69989154HCID 69989154, compound

Product 1

HCID 57135847HCID 57135847, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine N,N′-dibenzyl-2-aminomalonamide trifluoroacetic acid salt (0.41 g, 1.04 mmol), (R)-2-bromo-3-phenylpropionic acid (0.262 g, 1.15 mmol), N-methylmorpholine (0.23 mL, 2.08 mmol), 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (0.22 g, 1.15 mmol), and 1 -hydroxybenztriazole hydrate (0.155 g, 1.15 mmol) in dichloromethane (5 mL). After 18 hours, extract with an aqueous 5% sulfuric acid solution, a saturated sodium bicarbonate solution, and then brine. Dry the organic layer 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.

Workup

  1. extractionextract with an aqueous 5% sulfuric acid solution
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give a residue

Sources & evidence

ORD record
ord-ff90cc5c79044f6d9a1786a54b26e194
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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