Triethylamine → HCID 56990475, compound

HRID 2165287Notes

Reaction equation

HRID 2165287 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[N:11]([OH:14])[C:10]1=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]([O:20][CH2:21][C:22]([O:24][CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:23])=[O:19].C(N(CC)CC)C>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[N:11]([O:14][CH2:17][C:18]([O:20][CH2:21][C:22]([O:24][CH:25]([CH2:26][CH3:27])[CH2:28][CH3:29])=[O:23])=[O:19])[C:10]1=[O:15])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamateHCID 57264773HCID 57264773, compound

Product 1

HCID 56990475HCID 56990475, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3S-trans)-3-[(t-Butyloxycarbonyl)amino]-1- hydroxy-4-methyl-2-azetidinone (21.6 g) was dissolved in 250 ml of dimethylformamide. At 0° C. 26.7 g of bromoacetic acid. [(3-pentyloxy)carbonyl]-methyl ester was added, followed by 17 ml of triethylamine. The mixture was stirred overnight, and the dimethylformamide was evaporated in vacuo. The oily residue was dissolved in 300 ml of ethyl acetate, washed with ice-cold NaHCO3 solution and then washed three times with ice water. After drying over MgSO4, the solvent was evaporated in vacuo yielding 35.6 g of the title compound as an oil.

Workup

  1. customAt 0° C
  2. customthe dimethylformamide was evaporated in vacuo
  3. dissolutionThe oily residue was dissolved in 300 ml of ethyl acetate
  4. washwashed with ice-cold NaHCO3 solution
  5. washwashed three times with ice water
  6. dry with materialAfter drying over MgSO4
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-581da299c112427c8c9adbdc166c91d4
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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