Hydrochloric Acid → HCID 11856575, compound

HRID 1461251Notes

Reaction equation

HRID 1461251 reaction equation
[NH2:1][C@H:2]1[CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[CH2:3]1.C(N(CC)CC)C.[C:17]([S:20][CH2:21][CH:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23](Cl)=[O:24])(=[O:19])[CH3:18].Cl>C(#N)C.O>[C:17]([S:20][CH2:21][CH:22]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:23]([NH:1][C@H:2]1[CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[CH2:3]1)=[O:24])(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chlorideHCID 18603542(S)-4-Aminoazepan-2-one

Product 1

HCID 11856575HCID 11856575, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Combine 3(S)-amino-ε-caprolactam (1.00 g, 7.8 mmol) and triethylamine (0.87 g, 8.6 mmol) in acetonitrile (40ml) and H2O (20 ml). Add dropwise 2-acetylthiomethyl-3-phenylpropionyl chloride. After 30 min, add 1.0N HCl (13 ml), extract with ethyl acetate (EtOAc), dry and concentrate. Chromatograph on silica, eluting with 3%MeOH/CH2Cl2 to obtain the title compound as a foam. MS: M+1=349.

Workup

  1. extractionextract with ethyl acetate (EtOAc)
  2. customdry
  3. concentrationconcentrate
  4. washChromatograph on silica, eluting with 3%MeOH/CH2Cl2

Sources & evidence

ORD record
ord-abd8c7d873d240f08481e4617990aa03
Source dataset
uspto-grants-1991_12
Patent number
US05075302

Reaction notes

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