Lithium Hydroxide → HCID 69319218, compound

HRID 2389507Notes

Reaction equation

HRID 2389507 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[S:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23](=[O:25])[CH3:24])[CH:20]=[CH:19][C:18]=1[O:26][CH3:27].[OH-].[Li+]>C1COCC1>[C:23]([C:21]1[CH:20]=[CH:19][C:18]([O:26][CH3:27])=[C:17]([CH:22]=1)[CH2:16][S:15][C:6]1[N:5]([CH2:4][C:3]([OH:28])=[O:2])[C:9]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=2[N:7]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 91335761HCID 91335761, compound

Product 1

HCID 69319218HCID 69319218, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl[2-(5-acetyl-2-methoxy-benzylsulfanyl)-6-fluoro-benzoimidazol-1-yl]-acetate (Precursor 6-F-H-11b, 11.3 mg, 0.029 mmol) in dry THF (0.3 ml) is added some 1 N aqueous lithium hydroxide solution (0.140 ml, 5 eq.). The resulting biphasic solution is allowed to stir 1 h at rt. The solvents are removed in vacuo, water is added as well as 1N HCl in water so as to set the pH of the aqueous solution to pH=1. The resulting acidic aqueous phase is extracted three times with AcOEt. The organic phase is dried over Na2SO4 and the solvent removed in vacuo and the product was dried under high vacuum. This yields the title compound (6 mg) in 55% as a greyish solid: tR=0.95 min (LC-3), ESI-MS (pos.): m/z 388.89 [M+H]+, ESI-MS (neg.): m/z 387.10 [M−H]+; 1H-NMR (DMSO-d6): δ (ppm) 2.40 (s, 3H, COCH3), 3.87 (s, 3H, OCH3), 4.49 (s, 2H, SCH2), 4.82 (s, 2H, CH2CO2), 7.01 (t, 1Harom), 7.09 (d, 1Harom), 7.42 (d, 1Harom), 7.53 (dd, 1Harom), 7.86 (d, 1Harom), 7.98 (s, 1Harom).

Workup

  1. customThe solvents are removed in vacuo, water
  2. additionis added as well as 1N HCl in water so as
  3. extractionThe resulting acidic aqueous phase is extracted three times with AcOEt
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customthe product was dried under high vacuum

Sources & evidence

ORD record
ord-ae37fd1065684979a6b8b1b942ac9bd0
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

Loading…