HCID 23501853, compound → HCID 23501772, compound

HRID 1835605Notes

Reaction equation

HRID 1835605 reaction equation
C1(COC([NH:11][CH:12]([CH3:63])[C:13]([O:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([CH:22]2[CH2:31][CH2:30][C:29]3[C:24](=[C:25]([CH2:60][CH2:61][CH3:62])[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][C:37]4[CH:42]=[C:41]([O:43]CC5C=CC=CC=5)[C:40]([C:51]5[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=5)=[CH:39][C:38]=4[CH2:58][CH3:59])=[CH:27][CH:28]=3)[O:23]2)=[O:21])=[O:14])=O)C=CC=CC=1>CO.C(Cl)(Cl)Cl.[Pd]>[NH2:11][CH:12]([CH3:63])[C:13]([O:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([CH:22]1[CH2:31][CH2:30][C:29]2[C:24](=[C:25]([CH2:60][CH2:61][CH3:62])[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][C:37]3[C:38]([CH2:58][CH3:59])=[CH:39][C:40]([C:51]4[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=4)=[C:41]([OH:43])[CH:42]=3)=[CH:27][CH:28]=2)[O:23]1)=[O:21])=[O:14]

Participants

4

Reactant 1

HCID 23501853HCID 23501853, compound

Product 1

HCID 23501772HCID 23501772, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584188Chloroform methanolSolvent

Procedure

3-((7-(3-(2-ethyl-4-(4-fluorophenyl)-5-(phenylmethyloxy)phenoxy)propoxy)-8-propylchroman-2-yl)carbonylamino)propyl 2-((phenylmethoxy)carbonylamino)propanoate (125 mg) is dissolved in methanol/chloroform (2:1, 7 mL) with 50 mg 10% Pd/C catalyst. Hydrogen gas is bubbled in for 3 hours, when the mixture is filtered through Celite® and concentrated to yield 88 mg of product as a white crunchy foam. Mass Spec (EI) m/z=637.5 (M+H)

Workup

  1. customHydrogen gas is bubbled in for 3 hours, when the mixture
  2. filtrationis filtered through Celite®
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b4286ce128f74fa7ad8ef165ae852917
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Reaction notes

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