HCID 6475368, compound → HCID 474906, compound

HRID 1602078Notes

Reaction equation

HRID 1602078 reaction equation
[CH3:1][CH2:2][C@@H:3]1[NH:46][C:44](=[O:45])[CH:43]([C@H:47]([OH:54])[C@@H:48]([CH2:50]/[CH:51]=[CH:52]/[CH3:53])[CH3:49])[N:42]([CH3:55])[C:40](=[O:41])[C@H:39]([CH:56]([CH3:58])[CH3:57])[N:38]([CH3:59])[C:36](=[O:37])[C@H:35]([CH2:60][CH:61]([CH3:63])[CH3:62])[N:34]([CH3:64])[C:32](=[O:33])[C@H:31]([CH2:65][CH:66]([CH3:68])[CH3:67])[N:30]([CH3:69])[C:28](=[O:29])[C@@H:27]([CH3:70])[NH:26][C:24](=[O:25])[C@H:23]([CH3:71])[NH:22][C:20](=[O:21])[C@H:19]([CH2:72][CH:73]([CH3:75])[CH3:74])[N:18]([CH3:76])[C:16](=[O:17])[C@H:15]([CH:77]([CH3:79])[CH3:78])[NH:14][C:12](=[O:13])[C@H:11]([CH2:80][C:81]([OH:84])([CH3:83])[CH3:82])[N:10]([CH3:85])[C:8](=[O:9])[CH2:7][N:6]([CH3:86])[C:4]1=[O:5].[H][H]>C(O)C.[Pd]>[CH3:53][CH2:52][CH2:51][CH2:50][C@H:48]([C@@H:47]([OH:54])[CH:43]1[N:42]([CH3:55])[C:40](=[O:41])[C@H:39]([CH:56]([CH3:57])[CH3:58])[N:38]([CH3:59])[C:36](=[O:37])[C@H:35]([CH2:60][CH:61]([CH3:62])[CH3:63])[N:34]([CH3:64])[C:32](=[O:33])[C@H:31]([CH2:65][CH:66]([CH3:67])[CH3:68])[N:30]([CH3:69])[C:28](=[O:29])[C@@H:27]([CH3:70])[NH:26][C:24](=[O:25])[C@H:23]([CH3:71])[NH:22][C:20](=[O:21])[C@H:19]([CH2:72][CH:73]([CH3:74])[CH3:75])[N:18]([CH3:76])[C:16](=[O:17])[C@H:15]([CH:77]([CH3:79])[CH3:78])[NH:14][C:12](=[O:13])[C@H:11]([CH2:80][C:81]([OH:84])([CH3:82])[CH3:83])[N:10]([CH3:85])[C:8](=[O:9])[CH2:7][N:6]([CH3:86])[C:4](=[O:5])[C@H:3]([CH2:2][CH3:1])[NH:46][C:44]1=[O:45])[CH3:49]

Participants

5

Reactant 2

HCID 6475368HCID 6475368, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 474906HCID 474906, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a suspension of 200 mg pre-hydrogenated 10% palladium/charcoal in 4 ml ethanol is added 1.2 g of [γ-hydroxy-MeLeu]4 -Ciclosporin (compound e) in 10 ml ethanol and hydrogenation is carried out at room temperature until no more hydrogen is taken up. After removal of the catalyst by filtration the solution is evaporated, yielding the title compound as an amorphous white powder, m.p. 154-156°, [α]D20 -225° (c=0.87 in CHCl3), -169° (c=0.70 in CH3OH).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration the solution
  3. customis evaporated

Sources & evidence

ORD record
ord-d2f0a7091f6b4342b4156ce3dea1c467
Source dataset
uspto-grants-1999_11
Patent number
US05981479

Reaction notes

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