HCID 15895330, compound → HCID 15895331, compound

HRID 1862631Notes

Reaction equation

HRID 1862631 reaction equation
C([O:8][C:9]1[CH:19]=[C:18]([CH2:20][CH2:21][NH:22][C@@H:23]([CH3:33])[C@H:24]([OH:32])[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH:17]=[CH:16][C:10]=1[O:11][CH2:12][C:13]([OH:15])=[O:14])C1C=CC=CC=1>C(O)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:19]=[C:18]([CH2:20][CH2:21][NH:22][C@@H:23]([CH3:33])[C@H:24]([OH:32])[C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)[CH:17]=[CH:16][C:10]=1[O:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 15895330HCID 15895330, compound

Product 1

HCID 15895331HCID 15895331, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-[2-benzyloxy-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetic acid (97 mg) in acetic acid (4 ml) was added 10% palladium carbon (wet, 50% water) (30 mg), and the mixture was stirred for 50 minutes at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and the solvent was removed under reduced pressure. After addition of ethyl acetate to the residue, collection of the resulting insoluble material by filtration gave 2-[2-hydroxy-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetic acid (77 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under reduced pressure
  3. additionAfter addition of ethyl acetate
  4. customto the residue, collection of the resulting insoluble material
  5. filtrationby filtration

Sources & evidence

ORD record
ord-48de22602f6b48dc92a092e34af9d48f
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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