N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo-2-oxetanyl)methyl]-4-pentenyl ester → N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo2-oxetanyl]-methyl]pentyl ester

HRID 2106852Notes

Reaction equation

HRID 2106852 reaction equation
[CH2:1]([C@@H:7]1[C:10](=[O:11])[O:9][C@H:8]1[CH2:12][CH:13]([O:18][C:19](=[O:28])[C@H:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[NH:21][CH:22]=[O:23])[CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H][H]>C1COCC1.[Pd]>[CH2:1]([C@@H:7]1[C:10](=[O:11])[O:9][C@H:8]1[CH2:12][CH:13]([O:18][C:19](=[O:28])[C@H:20]([CH2:24][CH:25]([CH3:26])[CH3:27])[NH:21][CH:22]=[O:23])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 86743995N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo-2-oxetanyl)methyl]-4-pentenyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86743994N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo2-oxetanyl]-methyl]pentyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10 mg of N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo-2-oxetanyl)methyl]-4-pentenyl ester in 0.5 ml of THF was treated with 2.5 mg of 5% Pd/C and hydrogenated. After the hydrogen uptake was finished the catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was chromatographed over silica gel with toluene/ethyl acetate (8:2) and there was obtained amorphous N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo-2-oxetanyl]-methyl]pentyl ester as a mixture of 2 diastereomers.

Workup

  1. filtrationwas filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed over silica gel with toluene/ethyl acetate (8:2)

Sources & evidence

ORD record
ord-c8d76123dc5d462d8057bf4c806162c2
Source dataset
uspto-grants-1990_06
Patent number
US04931463

Reaction notes

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