tert-butyl ((3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-(((E)-3-oxobut-1-en-1-yl)oxy)-1,5-dioxonan-3-yl)carbamate → HCID 86701246, compound

HRID 75752Notes

Reaction equation

HRID 75752 reaction equation
[CH2:1]([C@@H:8]1[C@@H:16]([O:17]/[CH:18]=[CH:19]/[C:20](=[O:22])[CH3:21])[C@H:15]([CH3:23])[O:14][C:13](=[O:24])[C@@H:12]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:11][O:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([C@@H:8]1[C@@H:16]([O:17][CH2:18][CH2:19][C:20](=[O:22])[CH3:21])[C@H:15]([CH3:23])[O:14][C:13](=[O:24])[C@@H:12]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:11][O:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([C@@H:8]1[C@@H:16]([O:17][CH2:18][CH2:19][CH:20]([OH:22])[CH3:21])[C@H:15]([CH3:23])[O:14][C:13](=[O:24])[C@@H:12]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:11][O:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 86701244tert-butyl ((3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-(((E)-3-oxobut-1-en-1-yl)oxy)-1,5-dioxonan-3-yl)carbamate

Product 2

HCID 86701246HCID 86701246, compoundYield 69%HCID 86701247tert-butyl ((3S,7S,8R,9S)-7-benzyl-8-(3-hydroxybutoxy)-9-methyl-2-oxo-1,5-dioxonan-3-yl)carbamateYield 14%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl ((3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-(((E)-3-oxobut-1-en-1-yl)oxy)-1,5-dioxonan-3-yl)carbamate (601 mg, 1.34 mmol, 1.00 equiv) in EtOAc (13 mL) was added 10% Pd/C (72 mg, 0.067 mmol, 0.050 equiv). The resulting suspension was stirred under an atmosphere of hydrogen (1 atm, balloon) overnight. The catalyst was then filtered through a pad of Celite® that was flushed with EtOAc. The filtrate was concentrated to provide an oil. Purification by automated silica gel column chromatography (10-50% EtOAc in hexanes) provided tert-butyl ((3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-(3-oxobutoxy)-1,5-dioxonan-3-yl)carbamate (417 mg, 69%) as well as tert-butyl ((3S,7S,8R,9S)-7-benzyl-8-(3-hydroxybutoxy)-9-methyl-2-oxo-1,5-dioxonan-3-yl)carbamate (86 mg, 14%).

Workup

  1. filtrationThe catalyst was then filtered through a pad of Celite® that
  2. customwas flushed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customto provide an oil
  5. customPurification by automated silica gel column chromatography (10-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b88b2ffde4c946f4ac8d5f2fc96238bf
Source dataset
uspto-grants-2014_09
Patent number
US08835462B2

Reaction notes

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