HCID 24971290, compound → (R)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)hexan-2-yl 2-methanamidoethanoate

HRID 2382222Notes

Reaction equation

HRID 2382222 reaction equation
[CH:1]([NH:3][CH2:4][C:5]([O:7][C@H:8]([CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:9][C@H:10]1[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:12](=[O:20])[O:11]1)=[O:6])=[O:2]>[Pd].C(Cl)Cl>[CH:1]([NH:3][CH2:4][C:5]([O:7][C@H:8]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:9][C@H:10]1[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:12](=[O:20])[O:11]1)=[O:6])=[O:2]

Participants

4

Reactant 1

HCID 24971290HCID 24971290, compound

Product 1

HCID 42606551(R)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)hexan-2-yl 2-methanamidoethanoateYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Prepared according to representative procedure described in Example 63, above. β-lactone 17f (6.2 mg, 0.018 mmol) and 5 wt % palladium on carbon (5 mg) in 2 mL of CH2Cl2 was stirred at ambient temperature for 12 h under H2 atmosphere. Filtration and chromatography (SiO2, 40% EtOAc:hexanes) gave the desired β-lactone 23b (5.8 mg, 95.1%).

Workup

  1. customPrepared
  2. filtrationFiltration and chromatography (SiO2, 40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-8f780103495e43d09d2be491d4db6fb9
Source dataset
uspto-grants-2012_09
Patent number
US08258321B2

Reaction notes

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