Dichloromethane → HCID 86743754, compound

HRID 1199582Notes

Reaction equation

HRID 1199582 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.[C:8]1(=[O:22])[N:12]([CH2:13][C:14](Cl)=[O:15])[C:11](=[O:17])[C:10]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:9]12.[CH2:23]([Cl:25])Cl>>[CH2:6]([N:3]1[C@H:4]([CH2:23][Cl:25])[C@H:13]([N:12]2[C:11](=[O:17])[C:10]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:9]3[C:8]2=[O:22])[C:14]1=[O:15])[C:7]1[CH:11]=[CH:10][CH:9]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-

Product 1

HCID 86743754HCID 86743754, compound

Procedure

A solution of 3.34 g of the product 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-5e445365ef9241fa8123dfd88498cdc8
Source dataset
uspto-grants-1990_02
Patent number
US04900728

Reaction notes

Loading…