Dichloromethane → HCID 69830927, compound

HRID 365837Notes

Reaction equation

HRID 365837 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 CH2Cl2 (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 CH2Cl2, which was dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with CH2Cl2 :MeOH 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 EtOH 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 CH2Cl2, which
  2. dry with materialwas dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on a silica gel column
  5. washeluting with CH2Cl2 :MeOH 10:5 to 10:11

Sources & evidence

ORD record
ord-773921483e904dc58a067509ec45085a
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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