Methanesulfonic Acid → HCID 86071577, compound

HRID 2363913Notes

Reaction equation

HRID 2363913 reaction equation
Cl.[NH2:2][CH2:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:8].[CH3:17][S:18]([OH:21])(=[O:20])=[O:19]>O.C(O)C>[CH3:17][S:18]([OH:21])(=[O:20])=[O:19].[NH2:2][CH2:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:8]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 6433082Hexaminolevulinate hydrochloride

Product 1

HCID 86071577HCID 86071577, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of hexyl 5-amino-4-oxopentanoate hydrochloride (1.0 g; 4.0 mmol) in water (5 ml) and 96% ethanol (5 ml) was passed through a column of Amberlyst A-26(OH) (2.1 g; 8.8 meq) into a solution of methanesulfonic acid (0.38 g; 4.0 mmol) in water (3 ml). The resin column was washed with 50% aq. ethanol (10 ml) and the combined eluents were evaporated to dryness. After drying overnight, the residue was purified by flash chromatography on a 170×25 mm silica gel 60 column eluted with acetonitrile (200 ml), 5 methanol in acetonitrile (500 ml), 7.5% methanol in acetonitrile (500 ml) and 10% methanol in acetonitrile (750 ml), collecting 27×50 ml fractions. Evaporation of fractions containing product gave 0.77 g (62%) residue, mp 132-134° C.

Workup

  1. washThe resin column was washed with 50% aq. ethanol (10 ml)
  2. customthe combined eluents were evaporated to dryness
  3. customAfter drying overnight
  4. customthe residue was purified by flash chromatography on a 170×25 mm silica gel 60 column
  5. washeluted with acetonitrile (200 ml), 5 methanol in acetonitrile (500 ml), 7.5% methanol in acetonitrile (500 ml)
  6. custom10% methanol in acetonitrile (750 ml), collecting 27×50 ml fractions
  7. customEvaporation of fractions
  8. additioncontaining product

Sources & evidence

ORD record
ord-370b300457e44074be21d2bc0e07cb60
Source dataset
uspto-grants-2014_04
Patent number
US08692014B2

Reaction notes

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