2-Methylbenzenesulfonic acid hydrate → HCID 21345163, compound

HRID 367084Notes

Reaction equation

HRID 367084 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]([F: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]([F:24])[N:3]=1

Participants

5

Reactant 2

HCID 124969952-Methylbenzenesulfonic acid hydrateHCID 21345162HCID 21345162, compound

Product 1

HCID 21345163HCID 21345163, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,6-Difluoro-3-(1-Cbz-2-(S)-azetidinylmethoxy)pyridine from Example 116b (640 mg, 1.9 mmol) was combined with 10% Pd on C (50 mg) and p toluenesulfonic acid monohydrate (1.1 g, 5.7 mmole) in 30 mL of EtOH, and the mixture was stirred under an H2 atmosphere for 16 hours. The mixture was concentrated, triturated with ether and then recrystallized from ethyl acetate/ether to yield 231 mg (32.4%) of the title compound: mp 140-143° C. 1H NMR (D2O 300 MHz) 6: 2.40 (s, 3H), 2.69 (m, 2H), 4.12 (m, 2H), 4.46 (d, J=4.5, 2H), 4.94 (m, 1H), 7.01 (m, 1H), 7.38 (d,J=8.0, 2H), 7.70 (d,J=8.0, 2H), 7.81 (m, 1H). MS (DCI/NH3) m/e 201 (M+H)+, 218 (M+NH4)+. Anal. calcd. for C9H10F2N2O.C7H8O3S: C, 51.61H, 4.87 N, 7.52 Found: C, 51.37 H, 4.89; N, 7.40. [α]D -1.44 (c 1, MeOH).

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated with ether
  3. customrecrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-2ad5dc2b84424a54bfe5826689db2a1c
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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