Triethylamine → HCID 67207110, compound

HRID 384524Notes

Reaction equation

HRID 384524 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[C:13]([F:20])[CH:12]=1.CCN(CC)CC.C(OC(Cl)=O)C(C)C.[BH4-].[Na+]>C1COCC1.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:19]=[CH:18][C:14]([CH2:15][OH:16])=[C:13]([F:20])[CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 67206182HCID 67206182, compound

Product 1

HCID 67207110HCID 67207110, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(benzothiazol-2-yloxy)-2-fluoro-benzoic acid (4.7 g, 16.1 mmol) in THF (100 mL) was added Et3N (2.5 mL, 17.7 mmol). The mixture was cooled to 0° C., and isobutylchloroformate (2.1 mL, 16.1 mmol) was added. The reaction mixture was stirred for 2 h, filtered, and concentrated. The residue was dissolved in THF (50 mL) and cooled to 0° C. Sodium borohydride (1.2 g, 32.2 mmol) was added and immediately followed by water (10 mL). The reaction mixture was then partitioned between EtOAc (50 mL) and brine (20 mL). The organic layer was separated, dried (Mg2SO4), filtered and concentrated. Purification by silica gel flash chromatography (0% to 60% EtOAc in hexanes) afforded the title compound as a colorless solid (3.3 g, 75%). MS (ESI): mass calcd. for C14H10FNO2S, 275.0; m/z found, 276.0 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.77 (d, J=8.1 Hz, 1H), 7.72 (dd, J=5.3, 2.7 Hz, 1H), 7.54 (t, J=8.4 Hz, 1H), 7.43 (td, J=7.6, 1.3 Hz, 1H), 7.32 (td, J=7.5, 1.2 Hz, 1H), 7.24-7.16 (m, 2H), 4.81 (d, J=5.8 Hz, 2H), 1.79 (t, J=6.1 Hz, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in THF (50 mL)
  4. temperaturecooled to 0° C
  5. customThe reaction mixture was then partitioned between EtOAc (50 mL) and brine (20 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (Mg2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel flash chromatography (0% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b65a362240e3462397461e8eeb3430b9
Source dataset
uspto-grants-2013_02
Patent number
US08367719B2

Reaction notes

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