HCID 86748104, compound → HCID 86748103, compound

HRID 1769280Notes

Reaction equation

HRID 1769280 reaction equation
C[C@@:2]([N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[NH:17][C:18](=[O:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([OH:28])(=[O:27])=[O:26])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([O-:5])=[O:4].[K]>O.C(O)C.[OH-].[Na+]>[S:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([NH:17][C:13]1[N:12]([C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4])[CH:16]=[CH:15][N:14]=1)=[O:29])([OH:28])(=[O:26])=[O:27]

Participants

5

Reactant 1

HCID 86748104HCID 86748104, compound

Product 1

HCID 86748103HCID 86748103, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

The potassium salt (22.5 g) was dissolved in a mixture of 200 mL H2O and 100 mL of ethanol. To this solution was added in NaOH (53 mL). The reaction was allowed to stir for 3 hours. The solvent ethanol was then removed in vacuo, and the aqueous acidified to pH=1.5 with 5N HCl. This solution was extracted with 10% ethanol/ethyl acetate (3×200 mL). The organic was dried (Na2SO4) and concentrated in vacuo to give 8.65 g (46% for two steps) of (R)-[(2-sulfobenzoyl)amino-1H-imidazol-1-yl]-octanoic acid as a white solid. MS.

Workup

  1. customThe solvent ethanol was then removed in vacuo
  2. extractionThis solution was extracted with 10% ethanol/ethyl acetate (3×200 mL)
  3. dry with materialThe organic was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1aef16020f364ac798440a913c85381e
Source dataset
uspto-grants-1995_01
Patent number
US05380866

Reaction notes

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