Hydrochloric Acid → 5-Hydroxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid

HRID 1747333Notes

Reaction equation

HRID 1747333 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][CH:5]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:20]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=3[S:22][CH:23]=2)[C:10]1=[O:29])[CH2:6][CH2:7][OH:8].CC1C2C(CN3C4C=CC=CC=4N(C4CCOC(=O)C4)C3=O)=CSC=2C=CC=1.[OH-].[Na+].Cl>O1CCOCC1>[OH:8][CH2:7][CH2:6][CH:5]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:20]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=3[S:22][CH:23]=2)[C:10]1=[O:29])[CH2:4][C:3]([OH:30])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59497341HCID 59497341, compoundHCID 59497594HCID 59497594, compound

Product 1

HCID 594972655-Hydroxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acidYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Hydroxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester and 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-3-(2-oxo-tetrahydro-pyran-4-yl)-1,3-dihydro-benzimidazol-2-one (51 mg) are dissolved in 1,4-dioxane (2.5 mL). Then 1.0 N NaOH solution (2.0 mL) is added and the mixture is stirred for 2 hr. Then 1.0 M HCl (3.0 mL) is added to make it acidic and the mixture is extracted with EtOAc (3×35 mL). The organic layers are combined, dried and concentrated to give crude product. Purification by preparative TLC using 7.5% MeOH in CH2Cl2 affords 43 mg (62% for two steps) of 5-Hydroxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid. LCMS (ESMS): m/z 411.07 (M+H+).

Workup

  1. extractionthe mixture is extracted with EtOAc (3×35 mL)
  2. customdried
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by preparative TLC

Sources & evidence

ORD record
ord-9bd1205a493d467195aea68319fba87f
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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