Dichloromethane → HCID 67804051, compound

HRID 2259197Notes

Reaction equation

HRID 2259197 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C(Cl)[Cl:31]>>[ClH:31].[F:22][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([F:21])[CH:18]=1)[O:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22857711HCID 22857711, compound

Product 1

HCID 67804051HCID 67804051, compound

Procedure

A 0.26 g (0.83 mmol) sample of the BOC-protected compound from step 7a was dissolved in 10 mL of 1:1 CH2Cl2 :TFA and stirred at room temperature until tlc showed no starting material. The solvent and reagent were removed by evaporation. The residue was suspended in 10% aqueous HCl, which was then adjusted to pH 12 with K2CO3, and the mixture was extracted with methylene chloride. The solvent was removed, and the residue was dried, then suspended in ether. Addition of ether/HCl precipitated the title product, which was wash with ether and dried to yield 0.62 g of the title compound. MS: 214(M+H)+, 231 (M+NH4)+, 248 (M+NH4NH3)+. NMR (D2O) δ: 1.87-2.33 (m, 4H), 3.41 (t, 2H, J=7), 4.05-4.12 (m, 2H), 4.38 (dd, 1H), 6.62-6.71 (m, 3 H). Anal. Calcd for C11H14ClF2NO.0.45 H2O: C, 51.25; H, 5.82; N 5.43; Found: C, 51.36; H, 5.35; N, 5.45.

Workup

  1. customThe solvent and reagent were removed by evaporation
  2. extractionthe mixture was extracted with methylene chloride
  3. customThe solvent was removed
  4. customthe residue was dried
  5. additionAddition of ether/HCl
  6. customprecipitated the title product, which
  7. washwas wash with ether
  8. customdried

Sources & evidence

ORD record
ord-6489d3d35c4142dd8961f3c4bfe28eac
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

Loading…