HCID 23501774, compound → HCID 23501851, compound

HRID 2228537Notes

Reaction equation

HRID 2228537 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:59])[CH2:13][CH2:14][NH:15][C:16]([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[C:21]([CH2:56][CH2:57][CH3:58])[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]3[CH:38]=[C:37]([O:39]CC4C=CC=CC=4)[C:36]([C:47]4[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=4)=[CH:35][C:34]=3[CH2:54][CH3:55])=[CH:23][CH:24]=2)[O:19]1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.C(Cl)(Cl)Cl.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:59])[CH2:13][CH2:14][NH:15][C:16]([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[C:21]([CH2:56][CH2:57][CH3:58])[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]3[C:34]([CH2:54][CH3:55])=[CH:35][C:36]([C:47]4[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=4)=[C:37]([OH:39])[CH:38]=3)=[CH:23][CH:24]=2)[O:19]1)=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 23501774HCID 23501774, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23501851HCID 23501851, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584188Chloroform methanolSolvent

Procedure

2-((tert-butoxy)carbonylamino)ethyl-3-((7-(3-(2-ethyl-4-(4-fluorophenyl)-5-(phenylmethoxy)phenoxy)propoxy)-8-propylchroman-2-yl)carbonylamino)propanoate (110 mg) was dissolved in methanol/chloroform (2:1, 5 mL) with 10% Pd/C (24 mg) and hydrogen gas bubbled in for 2 hours. The mixture was filtered through Celite®, rinsed with methanol, and concentrated under vacuum to afford 80 mg of 2-((tert-butoxy)carbonylamino)ethyl-3-((7-(3-(6-ethyl-4-(4-fluorophenyl)-3-hydroxyphenoxy)propoxy)-8-propylchroman-2-yl)carbonylamino)propanoate. Mass Spec (EI): 723.5 (M+H).

Workup

  1. custombubbled in for 2 hours
  2. filtrationThe mixture was filtered through Celite®
  3. washrinsed with methanol
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-30f047d58af24af1b38709479c2c3ba0
Source dataset
uspto-grants-2002_07
Patent number
US06416733B1

Reaction notes

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