Triethylamine → HCID 54054830, compound

HRID 1903009Notes

Reaction equation

HRID 1903009 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]1[CH:11]([CH2:12][OH:13])[CH2:10][C:9]1=[O:14])=[O:5])[CH3:2].C(N(CC)CC)C.[S:22](Cl)([CH3:25])(=[O:24])=[O:23]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]1[CH:11]([CH2:12][O:13][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:10][C:9]1=[O:14])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54399885HCID 54399885, compound

Product 1

HCID 54054830HCID 54054830, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.6 g. (8 mmoles) of 1-(2-ethoxycarbonylethyl)-4-(hydroxymethyl)-2-azetidinone prepared according to Example 5 are dissolved in 50 ml. of dry benzene, whereupon 2.2 ml. (1.16 g, 16 mmoles) of triethylamine are added to the solution, followed by a dropwise addition of 1.2 ml. (1.8 g., 16 mmoles) of mesyl chloride at 0° C., with stirring. After 30 minutes the salt is filtered off and the filtrate is evaporated in vacuo. The evaporation residue is dissolved in 50 ml. of chloroform, the solution is shaken with two 10-ml. portions of a 10% aqueous sodium carbonate solution and subsequently with three 10-ml. portions of water. The chloroform phase is dried over magnesium sulfate, filtered and the filtrate is evaporated. 1.9 g. (85%) of the named compound are obtained.

Workup

  1. dissolutionare dissolved in 50 ml
  2. additionfollowed by a dropwise addition of 1.2 ml
  3. filtrationAfter 30 minutes the salt is filtered off
  4. customthe filtrate is evaporated in vacuo
  5. dissolutionThe evaporation residue is dissolved in 50 ml
  6. dry with materialThe chloroform phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-b30144cf58a247e6987c7da1b7ba4630
Source dataset
uspto-grants-1984_03
Patent number
US04435322

Reaction notes

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