p-Toluenesulfonic acid → HCID 21345240, compound

HRID 367079Notes

Reaction equation

HRID 367079 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2[C:14](OCC2C=CC=CC=2)=O)=[CH:4][CH:3]=1.[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:29][CH:30]=1>CO>[S:31]([C:28]1[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][CH:27]=1)([OH:34])(=[O:33])=[O:32].[F:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2[CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 21345233HCID 21345233, compound

Product 1

HCID 21345240HCID 21345240, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by the procedure of example 98c, except substituting 6-fluoro-3-(1-Cbz-2-(S)-azetidinylmethoxy)pyridine for the R enantiomer thereof. The product was obtained as a white solid: mp 124-126° C.; [α]D =+15.93 (c 0.5, MeOH); 1H NMR (300 MHz, D2O) δ 7.92 (s, 1H), 7.68 (m, 3H), 7.38 (d, 2H, J=8.0 Hz), 7.11 (dd, 1H, J=2.5,8.5 Hz), 4.8 (br s, 1H), 4.45 (m, 2H), 4.27 (br s, 1H), 4.02 (br s, 1H), 2.99 (s, 3H), 2.68 (m, 2H), 2.40 (s, 3H); MS (CI/NH3); m/z 197 (M+H)+. Anal. Calcd for C10H13FN2O.TsOH: C, 55.42; H, 5.75; N, 7.60. Found: C, 55.33; H, 5.74; N, 7.59.

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-c66dadb8c160452e9fd0b3458dca8ae8
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

Loading…