HCID 54384889, compound → HCID 54331878, compound

HRID 2299694Notes

Reaction equation

HRID 2299694 reaction equation
[C:1]([O:5][C:6](=[O:43])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][CH:15]([NH:19][CH2:20][C@@H:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29]CC4C=CC=CC=4)=[C:25]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:24]=3)[OH:22])[CH2:14][C:13]=2[CH:42]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6](=[O:43])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][CH:15]([NH:19][CH2:20][C@H:21]([OH:22])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:24]=3)[CH2:14][C:13]=2[CH:42]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 54384889HCID 54384889, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54331878HCID 54331878, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-[8-[(2R)-2-(4-benzyloxy-3-methanesulfonylaminophenyl)-2-hydroxyethylamino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid tert-butyl ester (353 mg) and 10% palladium on activated carbon (50% wet, 100 mg) in methanol (5 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 3.5 hours. After filtration, the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=10:1 to 5:1) to give 2-[8-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylaminophenyl)ethylamino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid tert-butyl ester (268 mg).

Workup

  1. filtrationAfter filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=10:1 to 5:1)

Sources & evidence

ORD record
ord-272074d92a71402e9256f522c446910a
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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