Lithium hydroxide, monohydrate → HCID 59497654, compound

HRID 1747438Notes

Reaction equation

HRID 1747438 reaction equation
C[O:2][C:3](=[O:28])[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:24]3[N:20]([C:21]([CH3:26])=[C:22]([CH3:25])[CH:23]=3)[CH:19]=[CH:18][CH:17]=2)[C:7]1=[O:27].O.[OH-].[Li+]>C1COCC1.O.CO.C(Cl)Cl>[CH3:25][C:22]1[CH:23]=[C:24]2[N:20]([C:21]=1[CH3:26])[CH:19]=[CH:18][CH:17]=[C:16]2[CH2:15][N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:6]([CH2:5][CH2:4][C:3]([OH:28])=[O:2])[C:7]1=[O:27]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59497701HCID 59497701, compound

Product 1

HCID 59497654HCID 59497654, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of 3-[3-(2,3-dimethyl-indolizin-8-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-propionic acid methyl ester (110 mg, 0.29 mmol) in THF (5 ml) and water (1.5 ml) was added lithium hydroxide monohydrate (25 mg, 0.58 mmol). After 1.5 h the reaction appeared complete (LC-MS) and was subsequently concentrated. The remaining residue was diluted with water (˜12 ml) and acidified to pH˜5 using HOAc (˜5 drops). The resulting solid was dissolved into DCM and the layers were separated. The aqueous phase was extracted with DCM (1×) and the combined organics were concentrated. The remaining green residue was dissolved into a minimal volume of DCM and applied to a preparative TLC plate (1 mm). Eluted with 8% MeOH/DCM. The product-band was isolated and suspended in 5% MeOH/DCM. The silica gel was removed via filtration and washed with DCM. The combined filtrates were concentrated to give the desired product as a light green solid. LCMS (ESMS): m/z 364.24.

Workup

  1. concentration(LC-MS) and was subsequently concentrated
  2. additionThe remaining residue was diluted with water (˜12 ml)
  3. dissolutionThe resulting solid was dissolved into DCM
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted with DCM (1×)
  6. concentrationthe combined organics were concentrated
  7. dissolutionThe remaining green residue was dissolved into a minimal volume of DCM
  8. washEluted with 8% MeOH/DCM
  9. customThe product-band was isolated
  10. customThe silica gel was removed via filtration
  11. washwashed with DCM
  12. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-ed978c2648944f8d973d0faf1183d420
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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