Dichloromethane → HCID 53831084, compound

HRID 1769945Notes

Reaction equation

HRID 1769945 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH2:20][CH2:21][O:22][CH:23]([CH3:25])[CH3:24])[C:13](OC(C)(C)C)=[O:14])=[CH:7][CH:6]=1)C.FC(F)(F)C(O)=O.[CH2:34](Cl)[Cl:35]>>[CH:23]([O:22][CH2:21][CH2:20][N:12]([CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:3])=[O:26])=[CH:6][CH:7]=1)[C:13](=[O:14])[CH2:34][Cl:35])([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 54290387HCID 54290387, compound

Product 1

HCID 53831084HCID 53831084, compound

Procedure

7.1 g of the crude 4-[N-(2-isopropoxyethyl)-N-tert-butoxycarbonylaminomethyl]benzoic acid ethyl ester are dissolved in 70 ml of methylene chloride, and 40 ml of trifluoroacetic acid are added. The clear solution is left to stand overnight at room temperature and then concentrated by evaporation. The residue is taken up in methylene chloride, washed with aqueous ammonia solution (pH>9) and concentrated by evaporation. The oily/crystalline residue is dissolved in 50 ml of ethanol, and 50 ml of 2N sodium hydroxide solution are added. After stirring for 2 hours at 60°-65°, the solution is concentrated by evaporation and the residue is adjusted to pH 1 with water and 2N hydrochloric acid. The solution immediately becomes extremely cloudy and after about 5 minutes a precipitate forms. The mixture is concentrated by evaporation and the residue is heated briefly with 100 ml of ethanol. The solution is dried with magnesium sulfate, filtered over Hyflo and concentrated by evaporation. The crude crystalline material is suspended in 80 ml of tetrahydrofuran, and 3.2 g of chloroacetyl chloride are added. The suspension is stirred at room temperature for 14 hours, then concentrated to dryness by evaporation. The residue is dissolved in methylene chloride, washed with diluted hydrochloric acid, dried and concentrated by evaporation. Sticky, sparingly soluble crystals are obtained corresponding to 4-[N-(2-isopropoxyethyl)-N-chloroacetylaminomethyl]-benzoic acid.

Workup

  1. waitThe clear solution is left
  2. concentrationconcentrated by evaporation
  3. washwashed with aqueous ammonia solution (pH>9)
  4. concentrationconcentrated by evaporation
  5. dissolutionThe oily/crystalline residue is dissolved in 50 ml of ethanol
  6. addition50 ml of 2N sodium hydroxide solution are added
  7. concentrationthe solution is concentrated by evaporation
  8. waitThe solution immediately becomes extremely cloudy and after about 5 minutes
  9. concentrationThe mixture is concentrated by evaporation
  10. temperaturethe residue is heated briefly with 100 ml of ethanol
  11. dry with materialThe solution is dried with magnesium sulfate
  12. filtrationfiltered over Hyflo
  13. concentrationconcentrated by evaporation
  14. addition3.2 g of chloroacetyl chloride are added
  15. stirringThe suspension is stirred at room temperature for 14 hours
  16. concentrationconcentrated to dryness by evaporation
  17. dissolutionThe residue is dissolved in methylene chloride
  18. washwashed with diluted hydrochloric acid
  19. customdried
  20. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-6ad82899ac4a4512b81c96ef055ea537
Source dataset
uspto-grants-1995_01
Patent number
US05384319

Reaction notes

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