2-Formylamino-4-methyl-pentanoic Acid 1-(3-hexyl-4-oxo-oxetan-2-ylmethyl)-dodec-4-enyl Ester → 3-Hexyl-4-((R)-2-hydroxytridecyl)-2-oxetanone, (3S,4S)-

HRID 2382223Notes

Reaction equation

HRID 2382223 reaction equation
[CH2:1]([CH:7]1[C:10](=[O:11])[O:9][CH:8]1[CH2:12][CH:13]([O:25]C(=O)C(NC=O)CC(C)C)[CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>[Pd].C1COCC1>[CH2:1]([C@H:7]1[C@H:8]([CH2:12][C@H:13]([OH:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:10]1=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 743768722-Formylamino-4-methyl-pentanoic Acid 1-(3-hexyl-4-oxo-oxetan-2-ylmethyl)-dodec-4-enyl Ester

Product 1

HCID 104282483-Hexyl-4-((R)-2-hydroxytridecyl)-2-oxetanone, (3S,4S)-Yield 104%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to representative procedure described in Example 63, above. E/Z-mixture of β-lactone 20a (5.8 mg, 0.016 mmol) and 5 wt % palladium on carbon (5 mg) in 2 mL of THF was stirred at ambient temperature for 12 h under H2 atmosphere. Filtration gave the desired β-lactone 13d (5.9 mg, 99%) as a white solid.

Workup

  1. customPrepared
  2. filtrationFiltration

Sources & evidence

ORD record
ord-1e76f1796e3c40febdc95df24e7190b8
Source dataset
uspto-grants-2012_09
Patent number
US08258321B2

Reaction notes

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