Nitrogen → HCID 67128536, compound

HRID 1189365Notes

Reaction equation

HRID 1189365 reaction equation
N#N.[CH3:3][O:4][C:5](=[O:19])[CH:6]([NH:9][C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:17])[CH3:16])[CH2:7]O.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>>[CH3:3][O:4][C:5]([CH:6]1[CH2:7][O:18][C:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:17])[CH3:16])=[N:9]1)=[O:19]

Participants

4

Reactant 3

HCID 947NitrogenHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 86664903HCID 86664903, compound

Product 1

HCID 67128536HCID 67128536, compound

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 3-hydroxy-2-(6-oxo-heptanoylamino)-propionic acid methyl ester (1.50 g, 6.12 mmol) in dry and degassed THF (24 mL) was added at −10° C. to a solution of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (1.79 g, 7.31 mmol) in dry and degassed THF (24 mL) and the resulting suspension was stirred at 0° C. for 1.5 h. The reaction mixture was then stirred at reflux for 1 h. The mixture was then allowed to cool down to rt and filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (97:3 EA-MeOH) gave the title compound as a light yellow oil. TLC: rf (97:3 EA-MeOH)=0.37. LC-MS-conditions 02: tR=0.62 min [M+H]+=228.53.

Workup

  1. customdegassed THF (24 mL)
  2. customin dry
  3. customdegassed THF (24 mL)
  4. stirringThe reaction mixture was then stirred
  5. temperatureat reflux for 1 h
  6. temperatureto cool down to rt
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customPurification of the residue by FC (97:3 EA-MeOH)

Sources & evidence

ORD record
ord-49b86f4a2cf2498398b02bca15fb138a
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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