HCID 131727922, compound → HCID 131727923, compound

HRID 2242657Notes

Reaction equation

HRID 2242657 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][C@H:8]([C:30]([N:32]1[CH2:36][CH2:35][C:34]([F:38])([F:37])[CH2:33]1)=[O:31])[C@H:9]([CH:15]1[CH2:20][CH2:19][C:18]([C:21]2[CH:22]=[CH:23][C:24]3[N:25]([N:27]=[CH:28][N:29]=3)[CH:26]=2)=[CH:17][CH2:16]1)[C:10]([N:12]([CH3:14])[CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6](=[O:39])[NH:7][C@H:8]([C:30]([N:32]1[CH2:36][CH2:35][C:34]([F:38])([F:37])[CH2:33]1)=[O:31])[C@H:9]([CH:15]1[CH2:16][CH2:17][CH:18]([C:21]2[CH:22]=[CH:23][C:24]3[N:25]([N:27]=[CH:28][N:29]=3)[CH:26]=2)[CH2:19][CH2:20]1)[C:10]([N:12]([CH3:14])[CH3:13])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 131727922HCID 131727922, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131727923HCID 131727923, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The material from Step C (0.79 g, 1.5 mmol) was placed under 1 atmosphere of hydrogen gas in the presence of 10% palladium on carbon (1.6 g) in methanol (40 mL). After 24 h, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give a mixture of cis and trans diastereomers. These diastereomers were separated by chiral HPLC (Chiralcel OD column eluting with 20% isopropanol in heptane) to afford the title compounds as single isomers (Analytical retention times: Diastereomer A Tr=11.8 min, Diastereomer B Tr=13.9 min. LC/MS 549.3 (M+1).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give
  4. additiona mixture of cis and trans diastereomers
  5. customThese diastereomers were separated by chiral HPLC (Chiralcel OD column eluting with 20% isopropanol in heptane)

Sources & evidence

ORD record
ord-0aece6dda0cf4e9789fea1c7bd5120be
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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