Trimethylsilylmethyl Azide → HCID 67169978, compound

HRID 877349Notes

Reaction equation

HRID 877349 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[C:9]#[CH:10])=[CH:4][CH:3]=1.[N:18]([CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[N+:19]=[N-:20].O=C1O[C@H]([C@H](CO)O)C(O)=C1O>O.C(O)(C)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([C:9]2[N:20]=[N:19][N:18]([CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:10]=2)[NH:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 150751Trimethylsilylmethyl AzideHCID 54670067L-Ascorbic AcidHCID 86668957HCID 86668957, compound

Product 1

HCID 67169978HCID 67169978, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 1.5 g (4.8 mmol) N-[(1R)-1-(4-bromophenyl)prop-2-ynyl]-2-methylpropane-2-sulfinamide in 10 mL water and 10 mL t-butanol was added 0.62 g (azidomethyl)(trimethyl)silane, 0.48 mL (0.48 mmol) 1.0M aqueous ascorbic acid solution, and 0.05 mL (0.05 mmol) 1.0M solution of aqueous copper (II) sulfate pentahydrate. After 24 h at room temperature, the reaction mixture was quenched with water, extracted three times with ethyl acetate, and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 25-100% EtOAc:hexane) afforded N-((S)-(4-bromophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)-2-methylpropane-2-sulfinamide. 1H NMR (CDCl3, 400 MHz) 7.51-7.47 (m, 2H); 7.35-7.30 (m, 2H); 7.06 (s, 1H); 5.68 (d, 1H, J=2.65 Hz); 4.58 (d, 1H, J=2.48 Hz); 3.81 (d, 2H, J=3.84 Hz); 1.24 (s, 9H); 0.12 (s, 9H). ES-MS [M+1]+=444.94.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted three times with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica gel, linear gradient 25-100% EtOAc:hexane)

Sources & evidence

ORD record
ord-688e6f4f521c425ab010e14c1a42eb52
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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