Ethyl Acetate → HCID 22679034, compound

HRID 1837786Notes

Reaction equation

HRID 1837786 reaction equation
C(N(CC)C(S[CH:7]([CH3:17])[C:8]([NH:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])=[O:9])=S)C.[CH3:20][C:21]1([CH3:30])[N:26]([O])[C:25]([CH3:29])([CH3:28])[CH2:24][CH2:23][CH2:22]1.C(OCC)(=[O:33])C>>[CH3:16][C:11]([NH:10][C:8](=[O:9])[CH:7]([O:33][N:26]1[C:21]([CH3:30])([CH3:20])[CH2:22][CH2:23][CH2:24][C:25]1([CH3:29])[CH3:28])[CH3:17])([CH3:15])[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 2724126TempoHCID 22679033HCID 22679033, compound

Product 1

HCID 22679034HCID 22679034, compoundYield 42%

Procedure

A mixture of 2-(2-diethylthiocarbamoylsulfanylpropionylamino)-2-methylpropionic acid (4.00 g; 0.0132 mol), TEMPO (2.04 g; 0.0132 mol) and ethyl acetate (35 ml) in a glass jar was purged with nitrogen gas for 20 minutes. The jar was then sealed and the mixture was irradiated with a 350 mn ultraviolet lamp (Sylvania 350 Blacklight F15T8/350BL available from Osram Sylvania, Danvers, Mass.) for 65 hours. The mixture was then concentrated under vacuum and diluted with diethyl ether (50 ml). The solid was isolated by filtration and was dried under vacuum to afford 1.75 g (42% yield) of 2-methyl-2-[2-(2,2,6,6-tetramethylpiperidin-1-yloxy)-propionylamino]-propionic acid.

Workup

  1. customwas purged with nitrogen gas for 20 minutes
  2. customThe jar was then sealed
  3. customthe mixture was irradiated with a 350 mn ultraviolet lamp (Sylvania 350 Blacklight F15T8/350BL available from Osram Sylvania, Danvers, Mass.) for 65 hours
  4. concentrationThe mixture was then concentrated under vacuum
  5. additiondiluted with diethyl ether (50 ml)
  6. customThe solid was isolated by filtration
  7. customwas dried under vacuum

Sources & evidence

ORD record
ord-d7c516d27f044608ab521e9f8ccd1503
Source dataset
uspto-grants-2004_08
Patent number
US06784264B2

Reaction notes

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