L-Leucine → N-(3,5-dinitrobenzoyl)leucine

HRID 485977

Reaction equation

HRID 485977 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[N+:10]([C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[C:16](Cl)=[O:17])([O-:12])=[O:11].C1OC1C>O1CCCC1>[N+:10]([C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[C:16]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:17])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 6106L-LeucineHCID 6378Propylene OxideHCID 74323,5-Dinitrobenzoyl chloride2×

Product 1

HCID 101111N-(3,5-dinitrobenzoyl)leucine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-Leucine (10 g) was suspended in 150 mL dry tetrahydrofuran and chilled in an ice bath while stirring under a nitrogen atmosphere. 3,5-Dinitrobenzoyl chloride (Table 2, Compound 13, 21 g) and propylene oxide (6.6 g) were added; the resulting heterogeneous mixture became clear after several minutes. The mixture was allowed to stir for 5 h, and was evaporated under reduced pressure to afford an oil which crystallized upon addition of 100 mL of cold dichloromethane. Filtration and drying of the resulting crystals afforded 3,5-dinitrobenzoyl-(S)-leucine, 14, as a white solid (20.64 g, 83% yield). 1H NMR (200 MHz, d6DMSO) δ: 0.95 (m,6 H), 1.75 (M,3 H), 4.25 (m,1 H), 9.00 (t,1 H), 9.17 (d,2 H), 9.41 (d,1 H).

Workup

  1. temperaturechilled in an ice bath
  2. waitthe resulting heterogeneous mixture became clear after several minutes
  3. stirringto stir for 5 h
  4. customwas evaporated under reduced pressure
  5. customto afford an oil which
  6. customcrystallized upon addition of 100 mL of cold dichloromethane
  7. filtrationFiltration
  8. customdrying of the resulting crystals

Sources & evidence

ORD record
ord-385eb14be42147ada7d63050fbe69141
Source dataset
uspto-grants-1994_03
Patent number
US05290440

Linked notes

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