HCID 59427277, compound → HCID 24768891, compound

HRID 502531Notes

Reaction equation

HRID 502531 reaction equation
[C:1]([N:4]([CH2:37][C@@H:38]1[O:42][C:41](=[O:43])[N:40]([C:44]2[CH:49]=[CH:48][C:47]([N:50]3[CH2:57][C:56]4[C:52](=[N:53][N:54]([CH3:58])[CH:55]=4)[CH2:51]3)=[C:46]([F:59])[CH:45]=2)[CH2:39]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:36])[C:11]1[CH:16]=[CH:15][C:14]([O:17][P:18]([O:28]CC2C=CC=CC=2)([O:20]CC2C=CC=CC=2)=[O:19])=[CH:13][CH:12]=1)=[O:6])(=[O:3])[CH3:2]>C1CC=CCC=1.C1COCC1.[Pd]>[C:1]([N:4]([CH2:37][C@@H:38]1[O:42][C:41](=[O:43])[N:40]([C:44]2[CH:49]=[CH:48][C:47]([N:50]3[CH2:57][C:56]4[C:52](=[N:53][N:54]([CH3:58])[CH:55]=4)[CH2:51]3)=[C:46]([F:59])[CH:45]=2)[CH2:39]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:36])[C:11]1[CH:16]=[CH:15][C:14]([O:17][P:18]([OH:28])([OH:20])=[O:19])=[CH:13][CH:12]=1)=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 59427277HCID 59427277, compound

Product 1

HCID 24768891HCID 24768891, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 123431,4-CyclohexadieneSolvent

Procedure

A suspension of 15 (1 equiv) and 10% Pd/C (1 weight equiv of 15) in 1,4-cyclohexadiene and THF is stirred at rt 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 646 (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-cbcc9f203d974a8ebf0b61568f265f8f
Source dataset
uspto-grants-2010_08
Patent number
US07776855B2

Reaction notes

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