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Acetic acid, azido-, ethyl ester → ethyl(4-{(S)-[(tert-butylsulfinyl)amino][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)acetate

HRID 877381
Notes
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Reaction equation

HRID 877381 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[CH3:10][C:11]([S:14]([NH:16][C@@H:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:22][N:21]=1)[C:18]#[CH:19])=[O:15])([CH3:13])[CH3:12].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].C(O)CCC.O>O>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][N:1]1[CH:19]=[C:18]([C@H:17]([NH:16][S:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([F:31])([F:29])[F:30])=[CH:22][N:21]=2)[N:3]=[N:2]1)[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 69480Acetic acid, azido-, ethyl esterHCID 22253497Water butanolHCID 23667548Sodium AscorbateHCID 866689592-methyl-N-{(1R)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]prop-2-ynyl}propane-2-sulfinamide

Product 1

HCID 131732597ethyl(4-{(S)-[(tert-butylsulfinyl)amino][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)acetate
Yield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 ml round bottom flask equipped with a magnetic stir bar were added ethyl azidoacetate (0.193 g, 1.495 mmol), 2-methyl-N-{(1R)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]prop-2-yn-1-yl}propane-2-sulfinamide (0.500 g, 1.495 mmol), freshly made 1.0 N sodium ascorbate (0.150 ml, 0.150 mmol), and 1.0 N Cu2SO4 (0.150 ml, 0.150 mmol) into 6.0 ml of a mixed solvent BuOH/H2O (1:1). The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by flash chromatography (SiO2, 50-80% ethyl acetate in hexanes, gradient) gave the title compound as a light yellow solid (0.365 g, 53%). 1H NMR (CDCl3, 400 MHz) δ 8.291 (d, J=2.93 Hz, 1H), 7.634 (s, 1H), 7.452 (d, J=8.79 Hz, 1H), 7.247 (ABq, J=3.03 Hz, 1H), 5.879 (d, J=5.50 Hz, 1H), 5.349 (d, J=5.31 Hz, 1H), 5.125 (ABq, J=7.49 Hz, 2H), 4.381 (q, J=7.87 Hz, 2H), 4.255 (q, J=7.14 Hz, 2H), 1.290 (t, J=7.14 Hz, 3H), 1.271 (s, 9H). ES-MS [M+1]+: 464.1.

Workup

  1. customTo a 50 ml round bottom flask equipped with a magnetic stir bar
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuum
  7. customPurification by flash chromatography (SiO2, 50-80% ethyl acetate in hexanes, gradient)

Sources & evidence

ORD record
ord-65a36dae87f042619714d4f9f65455cd
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987310B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes