Diethyl Ether → 2-Acetylthio-5-aminopentanoic acid

HRID 1447641Notes

Reaction equation

HRID 1447641 reaction equation
[C:1]([S:4][CH:5]([CH2:9][CH2:10][CH2:11][NH:12]C(OCC1C=CC=CC=1)=O)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].CCOCC>Br.C(O)(=O)C>[C:1]([S:4][CH:5]([CH2:9][CH2:10][CH2:11][NH2:12])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 203843142-Acetylthio-5-benzyloxycarbonylaminopentanoic acid

Product 1

HCID 203843272-Acetylthio-5-aminopentanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 2-acetylthio-5-benzyloxycarbonylaminopentanoic acid (1.6 g.) in 2 N hydrobromic acid in acetic acid (10 ml.) is kept at room temperature for thirty minutes. Ether is added to maximum precipitation and the supernatant is decanted. The residue is dissolved in water and applied to a column of Dowex 50 in the hydrogen cycle. The column is washed with water, and 2-acetylthio-5-aminopentanoic acid is eluted with M pyridine-acetic acid buffer pH 6.5.

Workup

  1. customthe supernatant is decanted
  2. dissolutionThe residue is dissolved in water
  3. washThe column is washed with water, and 2-acetylthio-5-aminopentanoic acid
  4. washis eluted with M pyridine-acetic acid buffer pH 6.5

Sources & evidence

ORD record
ord-eba4750ffd5543f988d3d97139d998eb
Source dataset
uspto-grants-1979_12
Patent number
US04177277

Reaction notes

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