Sodium Hydroxide → HCID 58644774, compound

HRID 15533Notes

Reaction equation

HRID 15533 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:25][CH2:26][CH3:27])(C)(C)C.[OH-].[Na+]>C(O)C.C(Cl)Cl>[C:21]([O:20][C:18]([NH:17][C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:28])=[O:5])[C:9]([CH2:25][CH2:26][CH3:27])=[N:10][C:11]=2[CH:16]=1)=[O:19])([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67199280(5-tert-Butoxycarbonylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 58644774HCID 58644774, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

The product of step d.) was dissolved in 3 mL ethanol, treated with 1 M NaOH (500 μL), and heated to 70° C. for one hour. The reaction was diluted in DCM and extracted with water. The aqueous layer was acidified with 1 M HCl and extracted with DCM. The organic layer was washed with water, concentrated and purified by preparative LCMS to give the title compound. MS: ESI (positive): 334 (M+H).

Workup

  1. extractionextracted with water
  2. extractionextracted with DCM
  3. washThe organic layer was washed with water
  4. concentrationconcentrated
  5. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-c0267d7a4d17472887b6e0ded77623d3
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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