Triethylamine → HCID 18781932, compound

HRID 1420536Notes

Reaction equation

HRID 1420536 reaction equation
C(N(CC)CC)C.[CH3:8][S:9][CH:10]1[N:13]([CH2:14][C:15]([OH:17])=O)[C:12](=[O:18])[CH2:11]1.ClC(OCC)=O.[CH2:25]([O:32][NH2:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)(Cl)Cl>[CH2:25]([O:32][NH:33][C:15](=[O:17])[CH2:14][N:13]1[CH:10]([S:9][CH3:8])[CH2:11][C:12]1=[O:18])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 102313O-BenzylhydroxylamineHCID 18781934HCID 18781934, compound

Product 1

HCID 18781932HCID 18781932, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-10 °C

Procedure

Triethylamine (2 ml) was added to a solution of (4-methylthio-2-oxo-azetidin-1-yl)acetic acid (1.67 g) in dry chloroform (15 ml) cooled to -10° C. After 5 mins ethyl chloroformate (1.6 ml) was added, then after a further 5 mins a solution of O-benzylhydroxylamine free base (1.67 g) in chloroform was added. The solution was allowed to warm to room temperature and stirred for 16 hours then washed with brine, dried (MgSO4) and evaporated. Chromatography of the residue on silica gel (petroleun ether/ethyl acetate) gave N-benzyloxy-(4-methylthio-2-oxo-azetidin-1-yl)acetamide as a clear gum (22% yield).

Workup

  1. temperatureto warm to room temperature
  2. washthen washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-ffeaae135f7f41008a5e966d2b0eec24
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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