Hydrochloric Acid → HCID 69314718, compound

HRID 2389496Notes

Reaction equation

HRID 2389496 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])(C)(C)C.C1COCC1.Cl>[OH-].[Na+].O>[C:24]([O:23][C:21]([NH:20][CH2:19][CH2:18][S:17][C:9]1[N:8]([CH2:7][C:6]([OH:28])=[O:5])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 91275966HCID 91275966, compound

Product 1

HCID 69314718HCID 69314718, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

tert-Butyl[2-(2-tert-butoxycarbonylamino-ethylsulfanyl)-benzoimidazol-1-yl]-acetate (Precursor V-02b, 28.5 mg, 0.07 mmol) is suspended in 0.2 M aqueous NaOH (2.1 ml), THF (3.95 ml) is then added and the initially turbid suspension becomes a clear solution. After 7 h, 1M aqueous HCl solution (420 μl) is added. The solution is diluted with water (10 ml) and extracted with dichloromethane (15 ml). The organic phase is dried over MgSO4 filtered over a fritted funnel and the solvents are evaporated in vacuo. Drying of the residue under high vacuum yields the title compound (19 mg) in 77% as a colourless solid: tR=1.74 min (LC-2), ESI-MS (pos.): m/z 352.17 [M+H]+, ESI-MS (neg.): m/z 350.20 [M−H]+.

Workup

  1. extractionextracted with dichloromethane (15 ml)
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered over a fritted funnel
  4. customthe solvents are evaporated in vacuo
  5. customDrying of the residue under high vacuum

Sources & evidence

ORD record
ord-f1f3b9546fc5497e97705b61898c736a
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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