Phenethylamine → HCID 18348138, compound

HRID 2269817Notes

Reaction equation

HRID 2269817 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].[Cl-].[Na+].[CH2:18]([NH2:26])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C[N:28]1[CH2:33][CH2:32]OCC1.Cl.C(N=C=NCCCN(C)C)C.O.ON1[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=2N=N1>C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC.O1CCCC1>[CH2:18]([NH:26][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:28][CH2:33][CH2:32][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:12])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

10

Reactant 6

HCID 1001PhenethylamineHCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 183481032-((tert-Butoxycarbonyl)amino)malonic acid

Product 1

HCID 18348138HCID 18348138, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine a mixture of t-butoxycarbonylaminomalonic acid and sodium chloride from Preparation 1.2 (5.0 g, 13.7 mmol), phenethylamine (4.32 mL, 34.3 mmol), and tetrahydrofuran (25 mL). Cool in an ice bath. Remove the ice bath. Add N-methylmorpholine (3.8 mL, 34.3 mmol), 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (6.58 g, 34.3 mmol), and 1-hydroxybenztriazole hydrate (4.63 g, 34.3 mmol). Allow to warm to ambient temperature. After 18 hours, dilute the reaction mixture with ethyl acetate, extract with an aqueous 5% sulfuric acid solution, a saturated sodium bicarbonate solution, and then brine. Dry the organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 2/1 ethyl acetate/hexane to give the title compound (84%).

Workup

  1. temperatureCool in an ice bath
  2. customRemove the ice bath
  3. extractionextract with an aqueous 5% sulfuric acid solution
  4. dry with materialDry the organic layers over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-623889f6341d44f3a5006baf9ca66748
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

Loading…