Acetonitrile → HCID 57042163, compound

HRID 1248635Notes

Reaction equation

HRID 1248635 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:10])[C@H:7]([CH3:9])[NH2:8])([CH3:4])[CH3:3].[C:11](#[N:13])[CH3:12]>>[O:5]=[C:2]([NH:8][C@H:7]([C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:10])[CH3:9])[CH2:1][CH2:12][CH:11]1[CH2:9][CH2:7][C:6](=[O:10])[NH:13]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 89016L-Alanine 1,1-dimethylethyl ester

Product 1

HCID 57042163HCID 57042163, compound

Conditions

Temperature
80 °C

Procedure

A solution of 7.0 g (0.05 mol) of dihydro-1H-3,5(2H,6H) dioxopyrrolizidine in 150 ml of acetonitrile is treated with 14.5 g (0.1 mol) L-alanine 1,1-dimethylethyl ester. The mixture is refluxed 24 hours. The solution is concentrated at reduced pressure and the resulting oil is chromatographed over silica gel using elution with 2.5% methanol in dichloromethane. After concentration at reduced pressure the oil is rechromatographed over silica gel using 19:1 dichloromethane:methanol. The eluate is concentrated at reduced pressure and heated at 80° C. to yield N-[1-oxo-3-(5-oxo-2-pyrrolidinyl)propyl]-L-alanine, 1,1-dimethylethyl ester as an analytically pure oil with the following characteristic proton NMR spectrum: 1H-NMR(CDCL3) 1.35 (d, 3H), 1.5 (s, 9H), 1.5-2.4 (m, 9H), 3.5-3.8 (m, 1H), 4.4 (m, 1H), 6.6-6.8 (m, 1H), 7.4-7.6 (m, 1H).

Workup

  1. temperatureThe mixture is refluxed 24 hours
  2. concentrationThe solution is concentrated at reduced pressure
  3. customthe resulting oil is chromatographed over silica gel using elution with 2.5% methanol in dichloromethane
  4. concentrationAfter concentration at reduced pressure the oil
  5. customis rechromatographed over silica gel using 19:1 dichloromethane
  6. concentrationThe eluate is concentrated at reduced pressure

Sources & evidence

ORD record
ord-8bd28d34388b472893c78d4b6f0b783d
Source dataset
uspto-grants-1985_06
Patent number
US04525476

Reaction notes

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