HCID 86584558, compound → HCID 22843300, compound

HRID 1794773Notes

Reaction equation

HRID 1794773 reaction equation
[N:1]([CH2:4][C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=1)[OH:6])=[N+]=[N-]>[Pd].CO>[NH2:1][CH2:4][C@@H:5]([C:7]1[CH:8]=[CH:9][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:12]=1)[OH:6]

Participants

4

Reactant 1

HCID 86584558HCID 86584558, compound

Product 1

HCID 22843300HCID 22843300, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-{4-[(1S)-azido-1-hydroxyethyl]phenyl}methanesulfonamide (which was obtained in Example 113) (0.55 g, 2.146 mmol), 10% Pd/C (0.03 g) and methanol (30 mL) was hydrogenated on a Parr shaker at 50 psi for 3 hours. The catalyst was removed by filtration through celite. The filtrate was concentrated under vacuo to give an off-white solid (0.48 g, 97% yield); MS (ES) m/z: 231 (MH+); 1H NMR (400 MHz, DMSO-d6) δ 2.57 (m, 2H), 2.94 (s, 3H), 3.4–4.2 (br, 2H), 4.38 (m, 1H), 4.6–5.8 (br, 2H), 7.23 (d, 2H), 7.26 (d, 2H).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationThe filtrate was concentrated under vacuo

Sources & evidence

ORD record
ord-334f0b1741324cecbcb5844af01003b3
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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