2-Methylbenzenesulfonic acid hydrate → HCID 21345175, compound

HRID 367089Notes

Reaction equation

HRID 367089 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][C@H:10]2[CH2:13][CH2:12][N:11]2C(O[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)=[CH:6][CH:5]=[C:4]([CH3:24])[N:3]=1.O.C1(C)C([S:32]([OH:35])(=[O:34])=[O:33])=CC=CC=1>CCO.[Pd]>[S:32]([C:21]1[CH:22]=[CH:23][C:18]([CH3:17])=[CH:19][CH:20]=1)([OH:35])(=[O:34])=[O:33].[F:1][C:2]1[C:7]([O:8][CH2:9][C@H:10]2[CH2:13][CH2:12][NH:11]2)=[CH:6][CH:5]=[C:4]([CH3:24])[N:3]=1

Participants

5

Reactant 2

HCID 124969952-Methylbenzenesulfonic acid hydrateHCID 21345173HCID 21345173, compound

Product 1

HCID 21345175HCID 21345175, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Fluoro-6-methyl-3-(1-Cbz-2-(R)-azetidinylmethoxy)pyridine from step 118a (500 mg, 1.51 mmol) was combined with 10% Pd/C (50 mg) and p toluenesulfonic acid monohydrate (600 mg, 3.15 mmole) in 30 mL of EtOH, and the mixture was stirred under an H2 atmosphere for 16 hours. The mixture was filtered, concentrated, the residue was triturated with ether, and the product was recrystallized from ethyl acetate/ether to yield 270 mg (50%) of the title compound. mp 158-160° C. 1H NMR (D2O 300 MHz) δ 2.40 (s, 6H), 2.65-2.70 (m, 2H), 4.07-4.18 (m, 2H), 4.42 (d, J=4.5, 2H), 4.91-95 (m, 1H), 7.15 (d, J=8.0, 1H), 7.37 (d,J=8.0, 2H), 7.55 (dd, J=8.0, 2.0, 1H), 7.69 (d,J=8.5, 2H). MS (DCI/NH3) m/e 197 (M+H)+ 214 (M+NH4)+. Anal. calcd. for C10H13FN2O.C7H8O3S.0.4 H2O: C, 54.36 H, 5.85 N, 7.46. Found: C, 54.48 H, 5.81; N, 7.28; [α]D +2.05 (c 1, MeOH).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was triturated with ether
  4. customthe product was recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-203a51a095f6446eaa92c295ee0036a1
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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