Benzylamine → HCID 18348128, compound

HRID 2269820Notes

Reaction equation

HRID 2269820 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([OH:15])=O)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[N:25]1[CH2:30][CH2:29]OCC1.Cl.C(N=C=NCCCN(C)C)C.O.ON1[C:49]2[CH:50]=C[CH:52]=[CH:53][C:48]=2N=N1>C(OCC)(=O)C.CCCCCC.ClCCl>[CH2:16]([NH:23][C:13](=[O:15])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:10]([NH:25][CH2:30][C:29]1[CH:52]=[CH:53][CH:48]=[CH:49][CH:50]=1)=[O:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 183481032-((tert-Butoxycarbonyl)amino)malonic acid

Product 1

HCID 18348128HCID 18348128, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine t-butoxycarbonylaminomalonic acid (0.438 g, 2.00 mmol), benzylamine (0.436 mL, 4.0 mmol), and dichloromethane (10 mL). Add N-methylmorpholine (0.55 mL, 5.00 mmol) ), 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (0.96 g, 5.0 mmol), and 1-hydroxybenztriazole hydrate (0.67 g, 5.0 mmol). After 18 hours, concentrate 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. Dry the organic layer 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 (52%).

Workup

  1. concentrationconcentrate in vacuo
  2. additiondilute
  3. customthe concentrated reaction mixture with ethyl acetate
  4. extractionextract with an aqueous 5% sulfuric acid solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-fc152552e0ae4296b105f8bf4ca434f2
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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