Benzyl Alcohol → HCID 66932807, compound

HRID 1365556Notes

Reaction equation

HRID 1365556 reaction equation
[BrH:1].[NH2:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>Br>[BrH:1].[NH2:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([O:9][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 50943228HCID 50943228, compound

Product 1

HCID 66932807HCID 66932807, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideCatalyst

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 5-amino-4-oxopentanoic acid hydrobromide (1.60 g, 7.5 mmol), benzyl alcohol (15 ml), and 48% hydrobromic acid (8 drops) was heated to 80° C. (bath temperature) for 2 days. The mixture was cooled to room temperature and excess benzyl alcohol was removed with a rotary evaporator at 0.12 mm Hg. The residue was titrated with diethyl ether (2×50 ml) and the residue was purified by flash chromatography on a 160×55 mm silica gel 60 column eluted sequentially with acetonitrile, 50 methanol in acetonitrile, and 10% methanol in acetonitrile. Fractions containing the product were combined and evaporated. The residue was titruated with diethyl ether (5×15 ml), filtered, and dried at 30° C. and 15 mm Hg to give 0.97 g (43%) tan powder, mp 62-67° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customexcess benzyl alcohol was removed with a rotary evaporator at 0.12 mm Hg
  3. customthe residue was purified by flash chromatography on a 160×55 mm silica gel 60 column
  4. washeluted sequentially with acetonitrile, 50 methanol in acetonitrile, and 10% methanol in acetonitrile
  5. additionFractions containing the product
  6. customevaporated
  7. filtrationfiltered
  8. customdried at 30° C.

Sources & evidence

ORD record
ord-d1d1138dd29e469bb410aa8d92546533
Source dataset
uspto-grants-2011_02
Patent number
US07888526B2

Reaction notes

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