Dichloromethane → HCID 69830927, compound

HRID 1780335Notes

Reaction equation

HRID 1780335 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([O:15][CH2:16][C@@H:17]2[CH2:20][CH2:19][N:18]2C(OC(C)(C)C)=O)[CH:12]=[N:13][CH:14]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([O-])(O)=O.[Na+].C(Cl)[Cl:34]>C(O)(C(F)(F)F)=O>[ClH:34].[ClH:34].[C:1]([C:9]1[CH:10]=[C:11]([O:15][CH2:16][C@@H:17]2[CH2:20][CH2:19][NH:18]2)[CH:12]=[N:13][CH:14]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 69830940HCID 69830940, compound

Product 1

HCID 69830927HCID 69830927, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A sample of 5-octynyl-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from step 63a in methylene chloride (3 mL) and TFA (2 mL) was stirred for 30 minutes at 0° C. The residue was neutralized with NaHCO3 to pH 8, then extracted with methylene chloride, which was dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with methylene chloride:methanol 10:5 to 10:11 to afford the free base of the title compound (178 mg). MS (CI/NH3) m/z 273 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ0.90 (m, 3H), 1.32 (m, 4H), 1.45 (m, 2H), 1.62 (m, 2H), 2.40 (m, 2H), 2.53 (m, 2H), 3.80 (m, 1H), 3.96 (m, 1H), 4.19 (m, 2H), 4.62 (m, 1H), 7.22 (m, 1H), 8.20 (m, 2H). The base was converted to the salt by treatment with hydrogen chloride saturated ethanol to give the title compound. mp 88°-90° C. MS (CI/NH3) m/z 273 (M+H)+. 1H NMR (D2O, 300 MHz) δ0.90 (m, 3H), 1.33 (m, 4H), 1.46 (m, 2H), 1.64 (m, 2H), 2.50 (t, J=2.9 Hz, 2H), 2.71 (m, 2H), 4.05-4.22 (m, 2H), 4.49 (d, J=4.4 Hz, 2H), 4.98 (m, 1H), 7.99 (m, 1H), 8.34 (s, 1H), 8.39 (d, J=2.6 Hz, 1H). Anal. Calcd for C17H24N2O·2.8 HCl: C, 54.53; H, 7.21; N, 7.48. Found: C, 54.25; H, 7.12; N, 7.63. [α]25D =-9.64° (c 2.08, MeOH).

Workup

  1. extractionextracted with methylene chloride, which
  2. dry with materialwas dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on a silica gel column
  5. washeluting with methylene chloride:methanol 10:5 to 10:11

Sources & evidence

ORD record
ord-b44b6cc6ce984d1892b78d355ab4b417
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

Loading…