Triethylamine → 3(S)-[2(S)-ACETYLTHIOMETHYL-3-(2-METHYLPHENYL)PROPIONYL]AMINO-delta-VALEROLACTAM

HRID 1461253Notes

Reaction equation

HRID 1461253 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:9][CH2:8][NH:7][C:5](=[O:6])[CH2:4]1.[C:10]([S:13][CH2:14][C@@H:15]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[C:16](O)=[O:17])(=[O:12])[CH3:11].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:10]([S:13][CH2:14][C@@H:15]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[C:16]([NH:2][C@H:3]1[CH2:9][CH2:8][NH:7][C:5](=[O:6])[CH2:4]1)=[O:17])(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 228417862(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acidHCID 228417873(S)-amino-delta-valerolactam hydrochloride

Product 1

HCID 539270853(S)-[2(S)-ACETYLTHIOMETHYL-3-(2-METHYLPHENYL)PROPIONYL]AMINO-delta-VALEROLACTAM

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepare 3(S)-amino-δ-valerolactam hydrochloride according to the procedure of J. Chem. Soc. Dalton Trans., 1987, p. 1127. Combine this lactam (0.29 g,2.0 mmol), 2(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid (0.50 g,2.0 mmol), triethylamine (0.03 g,3.0 mmol), and HOBT (0.30 g,2.0 mmol) in DMF (20 ml). Add DEC (0.38 g,2.0 mmol). Stir 18 hr, partition between EtOAc and H2O, dry and concentrate. Chromatograph on silica, eluting with 3% MeOH/CH2Cl2 to obtain the title compound as a foam, [α]D26 =-28.6° (EtOH)

Workup

  1. custompartition between EtOAc and H2O
  2. customdry
  3. concentrationconcentrate
  4. washChromatograph on silica, eluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-fa404e36b2754ef2bb0c448148dc24a5
Source dataset
uspto-grants-1991_12
Patent number
US05075302

Reaction notes

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