Hydrochloric Acid → HCID 58505590, compound

HRID 1917619Notes

Reaction equation

HRID 1917619 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[N:20]3[C:15]([CH:16]=[C:17]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:19]3)=[C:14]([C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:13]=2[CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([O:34]C)=[O:33])=[O:11])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2].Cl>CO.[OH-].[Na+]>[C:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[N:20]3[C:15]([CH:16]=[C:17]([CH:21]([CH3:22])[CH3:23])[CH:18]=[CH:19]3)=[C:14]([C:24](=[O:29])[C:25]([CH3:26])([CH3:27])[CH3:28])[C:13]=2[CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([OH:34])=[O:33])=[O:11])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58505552HCID 58505552, compound

Product 1

HCID 58505590HCID 58505590, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
23 °C

Procedure

A solution of methyl 3-{3-[(3-carbamoylphenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-(propan-2-yl)indolizin-2-yl}-2,2-dimethylpropanoate (111 mg, 0.220 mmol) in MeOH (2 mL) and 6M aqueous NaOH (2 mL) is heated at 70° C. for 1 h then cooled to 23° C., acidified to pH=1 with concentrated aqueous HCl, then partitioned between CH2Cl2 and brine. The organics are dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by reverse phase HPLC (35% CH3CN to 95% CH3CN in 0.1% TFA in water) gives the title compound (20 mg, 19%).

Workup

  1. custompartitioned between CH2Cl2 and brine
  2. dry with materialThe organics are dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude by reverse phase HPLC (35% CH3CN to 95% CH3CN in 0.1% TFA in water)

Sources & evidence

ORD record
ord-3d4fc3c046a74ab5bb99629653472d99
Source dataset
uspto-grants-2013_12
Patent number
US08618300B2

Reaction notes

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