Benzyl Alcohol → HCID 178468090, compound

HRID 654992Notes

Reaction equation

HRID 654992 reaction equation
O=[C:2]([C@@H:14]([CH3:26])[CH2:15][O:16][CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.C(N(CC)CC)C.[CH2:43]([OH:50])[C:44]1C=CC=CC=1>C(Cl)(Cl)Cl>[C:43]([C:3](=[C:2]([NH:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:14]([CH3:26])[CH2:15][O:16][CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])(=[O:50])[CH3:44]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 7504BenzylamineHCID 11130Triethylamine hydrochlorideHCID 14348512HCID 14348512, compound

Product 1

HCID 178468090HCID 178468090, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl (S)-3-oxo-4-methyl-5-benzyloxymethoxypentanoate (140 mg; 0.39 mmole) was dissolved in benzyl alcohol (0.9 ml), and molecular sieve 3A (0.2 g), benzylamine (50 mg; 0.47 mmole) and triethylamine hydrochloride (54 mg; 0.39 mmole) were added thereto, followed by stirring at 80° C. for 10 hours. The reaction mixture was diluted with chloroform (10 ml), and after removal of insoluble materials such as molecular sieve by filtration, the filtrate was washed with water. The organic layer was dried over anhydrous magnesium sulfate, followed by removal of the solvent under reduced pressure. Then, benzyl alcohol was removed under reduced pressure, and the residue was dissolved in dry toluene. Gaseous ketene was introduced therein at room temperature. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give benzyl (R)-2-acetyl-3-benzylamino-4-methyl-5-benzyloxymethoxy-2-pentenoate.

Workup

  1. customafter removal of insoluble materials such as molecular sieve
  2. filtrationby filtration
  3. washthe filtrate was washed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customfollowed by removal of the solvent under reduced pressure
  6. customThen, benzyl alcohol was removed under reduced pressure
  7. dissolutionthe residue was dissolved in dry toluene
  8. additionGaseous ketene was introduced
  9. customat room temperature
  10. customAfter completion of the reaction
  11. concentrationthe reaction mixture was concentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b6ccad03ac72414ab462bdf7859fd294
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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