Hydrochloric Acid → HCID 90787766, compound

HRID 643069Notes

Reaction equation

HRID 643069 reaction equation
[CH2:1]([C@H:8]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C@@H:9]([OH:32])[CH2:10][N:11](CC1C=CC=CC=1)[NH:12][C:13](=[O:24])[C@@H:14]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[H][H]>CO.[OH-].[OH-].[Pd+2]>[CH2:1]([C@H:8]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C@@H:9]([OH:32])[CH2:10][NH:11][NH:12][C:13](=[O:24])[C@@H:14]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68294422HCID 68294422, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90787766HCID 90787766, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 5F (0.115 g, 0.2 mmol) in methanol (2 mL) was treated with Pd(OH)2 (38 mg) and 4N HCl (52 μL, 1 equivalent) and a hydrogen balloon at 25° C. for 3.5 hrs. The solvents were evaporated, and the crude residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and the solvents were evaporated to give 90 mg (93%) of the title compound.

Workup

  1. customThe solvents were evaporated
  2. customthe crude residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents were evaporated

Sources & evidence

ORD record
ord-b3c6f9a0da07475d9f539f24956a243c
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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