HCID 59427266, compound → HCID 24768889, compound

HRID 502530Notes

Reaction equation

HRID 502530 reaction equation
[C:1]([N:4]([CH2:38][C@@H:39]1[O:43][C:42](=[O:44])[N:41]([C:45]2[CH:50]=[CH:49][C:48]([N:51]3[CH2:58][C:57]4[C:53](=[N:54][N:55]([CH3:59])[CH:56]=4)[CH2:52]3)=[C:47]([F:60])[CH:46]=2)[CH2:40]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:37])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][P:19]([O:29]CC2C=CC=CC=2)([O:21]CC2C=CC=CC=2)=[O:20])=[CH:13][CH:12]=1)=[O:6])(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([N:4]([CH2:38][C@@H:39]1[O:43][C:42](=[O:44])[N:41]([C:45]2[CH:50]=[CH:49][C:48]([N:51]3[CH2:58][C:57]4[C:53](=[N:54][N:55]([CH3:59])[CH:56]=4)[CH2:52]3)=[C:47]([F:60])[CH:46]=2)[CH2:40]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:37])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][P:19]([OH:29])([OH:21])=[O:20])=[CH:13][CH:12]=1)=[O:6])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 59427266HCID 59427266, compound

Product 1

HCID 24768889HCID 24768889, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 13 (1 equiv) and 10% Pd/C (1 weight equiv of 13) in methanol is hydrogenated in a Parr shaker at 30 psi for 6 h. The reaction mixture is filtered, concentrated in vacuo, purified directly by HPLC (C-18 column, 0-100% gradient elution, MeCN:H2O), and fractions containing product are lyophilized to give the title compound. Theoretical MS 662 (M+1)+

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated in vacuo
  3. custompurified directly by HPLC (C-18 column, 0-100% gradient elution, MeCN:H2O), and fractions
  4. additioncontaining product

Sources & evidence

ORD record
ord-be5c0c6e15b2415181f591aa15e8d620
Source dataset
uspto-grants-2010_08
Patent number
US07776855B2

Reaction notes

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