Lithium hydroxide, monohydrate → HCID 59497497, compound

HRID 1747352Notes

Reaction equation

HRID 1747352 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:26][Si](C(C)(C)C)(C)C)=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[C:7]1=[O:34].O.[OH-].[Li+]>C1COCC1.O>[OH:26][C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[C:16]([CH2:15][N:8]1[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]([CH2:5][CH2:4][C:3]([OH:35])=[O:2])[C:7]1=[O:34])=[CH:17][CH:18]=[CH:19]2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59497299HCID 59497299, compound

Product 1

HCID 59497497HCID 59497497, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-{3-[6-(tert-Butyl-dimethyl-silanyloxy)-naphthalen-1-ylmethyl]-2-oxo-2,3-dihydro-benzimidazol-1-yl}-propionic acid methyl ester (200 mg, 0.41 mmol) in THF (7 ml) and water (1 ml) was added lithium hydroxide monohydrate (26 mg, 0.61 mmol) at ambient temperature. Upon complete consumption of the starting material the reaction was diluted with water, ethyl acetate and 6N HCl (adjusted to pH=2). The layers were separated and the aqueous phase was extracted once with ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated. The remaining residue was diluted with acetonitrile (3 ml) and allowed to stand over night. The resulting precipitated product was collected via filtration, washed with acetonitrile and dried on house vacuum to give 15 mg (10%) of the desired product. LCMS (ESMS): m/z 363.38 (M+H+).

Workup

  1. customUpon complete consumption of the starting material the reaction
  2. additionwas diluted with water, ethyl acetate and 6N HCl (adjusted to pH=2)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted once with ethyl acetate
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionThe remaining residue was diluted with acetonitrile (3 ml)
  9. waitto stand over night
  10. customThe resulting precipitated product
  11. filtrationwas collected via filtration
  12. washwashed with acetonitrile
  13. customdried on house vacuum

Sources & evidence

ORD record
ord-79168486105a461290f9950fc966ecc6
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…