Triethylamine → HCID 86743754, compound

HRID 345644Notes

Reaction equation

HRID 345644 reaction equation
[Cl:1][CH2:2][CH:3]=[N:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:19]1(=[O:33])[N:23]([CH2:24][C:25](Cl)=[O:26])[C:22](=[O:28])[C:21]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:20]12>C(Cl)Cl>[CH2:5]([N:4]1[C@H:3]([CH2:2][Cl:1])[C@H:24]([N:23]2[C:22](=[O:28])[C:21]3=[CH:29][CH:30]=[CH:31][CH:32]=[C:20]3[C:19]2=[O:33])[C:25]1=[O:26])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 13958033HCID 13958033, compound

Product 1

HCID 86743754HCID 86743754, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.34 g of the product of Step A in 20 ml of methylene chloride was cooled to -50° C. and 2.8 ml of triethylamine were added all at once. A solution of 4 g of phthalimidoacetic acid chloride in 20 ml of methylene chloride was added thereto over 20 minutes. The mixture was stirred for one hour at 0° to -5° C. and was then poured into a decanting flask. The decanted organic phase was washed with 50 ml of demineralized water and 5 ml of a molar aqueous solution of sodium bicarbonate, and then twice with 30 ml of demineralized water. The wash water was re-extracted with 20 ml of methylene chloride and the combined organic phases were dried, rinsed and evaporated to dryness under vacuum. The 6 g of residue were chromatographed over silica gel and eluted with methylene chloride containing 5% ether. The fraction with an Rf=0.45 was evaporated to dryness and the residue was triturated with 10 ml of ether. The separated product was rinsed three times with 2 ml of ether and dried under vacuum to obtain 1.25 g of cis N-benzyl-3-phthalimido-4-chloromethyl-2-azetidinone melting at 149° C.

Workup

  1. additionwas then poured into a decanting flask
  2. washThe decanted organic phase was washed with 50 ml of demineralized water and 5 ml of a molar aqueous solution of sodium bicarbonate
  3. extractionThe wash water was re-extracted with 20 ml of methylene chloride
  4. customthe combined organic phases were dried
  5. washrinsed
  6. customevaporated to dryness under vacuum
  7. customThe 6 g of residue were chromatographed over silica gel
  8. washeluted with methylene chloride containing 5% ether
  9. customThe fraction with an Rf=0.45 was evaporated to dryness
  10. customthe residue was triturated with 10 ml of ether
  11. washThe separated product was rinsed three times with 2 ml of ether
  12. customdried under vacuum

Sources & evidence

ORD record
ord-c8e431a2f7fe48118f226112166f3f8c
Source dataset
uspto-grants-1991_10
Patent number
US05057512

Reaction notes

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