Water → HCID 58990126, compound

HRID 2261892Notes

Reaction equation

HRID 2261892 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:19]=[C:20]([N:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25])[CH:21]=1)[C:7]([NH:9][C@@H:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH3:11])=[O:8])=[N+:2]=[N-:3].O.O=[C:32]1O[C@H:37]([C@H](CO)O)[C:35]([O-])=[C:33]1[OH:34].[Na+]>CC(O)(C)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:33]([C:35]1[N:3]=[N:2][N:1]([C:4]2[CH:5]=[C:6]([CH:19]=[C:20]([N:22]([S:26]([CH3:29])(=[O:27])=[O:28])[CH2:23][CH2:24][CH3:25])[CH:21]=2)[C:7]([NH:9][C@@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])=[O:8])[CH:37]=1)(=[O:34])[CH3:32]

Participants

6

Reactant 3

HCID 962WaterHCID 23667548Sodium AscorbateHCID 86615674HCID 86615674, compound

Product 1

HCID 58990126HCID 58990126, compoundYield 1,025.5%

Reagents, catalysts & solvents 2

HCID 61499Cupric sulfate monohydrateCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of 0.15 g (0.36 mmol) 3-azido-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-[(methylsulfonyl)(propyl)amino]benzamide in 2 mL t-BuOH was added 1 mL water and 0.004 g (0.018 mmol) copper(II) sulfate hydrate and 0.007 g (0.036 mmol) sodium ascorbate. The heterogeneous reaction mixture was stirred at rt for 24 h, then diluted w. 75 mL EtOAc, washed with 50 mL water, 50 mL brine, dried over MgSO4, filtered, and concentrated. Purification by automated flash chromatography (40 g silica gel cartridge 20-100% EtAOc/hex over 15 min) afforded 0.18 g (100%) 3-(4-acetyl-1H-1,2,3-triazol-1-yl)-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-[(methylsulfonyl) (propyl)amino]benzamide as a foam. 1H NMR (CDCl3, 400 MHz) δ 8.57 (s, 1H), 8.11 (br t, J=1.83 Hz, 1H), 7.93 (t, J=2.02 Hz, 1H), 7.89 (br t, J=1.64 Hz, 1H), 7.38 (m, 2H) 7.06 (m, 2H), 6.52 (br d, J=7.50 Hz, 1H), 5.32 (quint, J=7.15 Hz, 1H), 3.74 (t, J=7.14 Hz, 2H), 2.93 (s, 3H), 2.76 (s, 3H), 1.64 (d, J=6.96 Hz, 3H), 1.54 (m, 2H), 0.93 (t, J=7.32 Hz, 3H). LCMS [M+H]+=488.1

Workup

  1. additiondiluted w
  2. wash75 mL EtOAc, washed with 50 mL water, 50 mL brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by automated flash chromatography (40 g silica gel cartridge 20-100% EtAOc/hex over 15 min)

Sources & evidence

ORD record
ord-b87307ff6e014162835960e7e5c4ae3f
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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