Caprolactam → 3(S)-[2(S)-ACETYLTHIOMETHYL-3-(2-METHYLPHENYL)PROPIONYL]-AMINO-epsilon-CAPROLACTAM

HRID 1461252Notes

Reaction equation

HRID 1461252 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([S:12][CH2:13][C@@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])[C:15](O)=[O:16])(=[O:11])[CH3:10].OC1C2N=N[NH:32]C=2C=CC=1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:9]([S:12][CH2:13][C@@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])[C:15]([C@H:3]1[CH2:4][CH2:5][CH2:6][NH:7][C:1](=[O:8])[CH:2]1[NH2:32])=[O:16])(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 7768CaprolactamHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 228417862(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 867453093(S)-[2(S)-ACETYLTHIOMETHYL-3-(2-METHYLPHENYL)PROPIONYL]-AMINO-epsilon-CAPROLACTAM

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3(S)-amino-:-caprolactam (0.28 g,2.2 mmol), 2(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid (0.50 g,2.0 mmol) and hydroxybenzotriazole (HOBT) (0.33 g,2.2 mmol) in DMF (10ml). Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (DEC) (0.42 g,2.2 mmol). Stir 18hr, partition between EtOAc and H2O, dry and concentrate. Chromatograph on silica, eluting with diethyl ether (Et2O) to obtain the title compound as a foam,[α]D26 =-31.3° (EtOH).

Workup

  1. custompartition between EtOAc and H2O
  2. customdry
  3. concentrationconcentrate
  4. washChromatograph on silica, eluting with diethyl ether (Et2O)

Sources & evidence

ORD record
ord-326c31f3e2a0435e9f99b46aad6ecba6
Source dataset
uspto-grants-1991_12
Patent number
US05075302

Reaction notes

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