Phenethylamine → HCID 18348138, compound

HRID 2269811Notes

Reaction equation

HRID 2269811 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]([NH2:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ClCCl.C[N:29]1[CH2:34][CH2:33]OCC1>C(OCC)(=O)C.CCCCCC>[CH2:16]([NH:24][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:29][CH2:34][CH2:33][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:12])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 183481032-((tert-Butoxycarbonyl)amino)malonic acid

Product 1

HCID 18348138HCID 18348138, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine t-butoxycarbonylaminomalonic acid (0.465 g, 2.12 mmol), phenethylamine (0.715 mL, 5.70 mmol), and dichloromethane (25 mL). Add N-methylmorpholine (0.752 mL, 6.85 mmol). Cool in an ice bath. Add benzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate complex (3.15 g, 6.85 mmol). Remove the ice bath and 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.

Workup

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

Sources & evidence

ORD record
ord-f30701b90b5c4cc38bf15b1d7bc3240c
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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