HCID 86678419, compound → HCID 86678418, compound

HRID 882653Notes

Reaction equation

HRID 882653 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:77])[C@H:19]([C:23]([NH:25][C@H:26]([C:30]([N:32]([C@@H:34]([C@@H:73]([CH3:76])[CH2:74][CH3:75])[C@H:35]([O:71][CH3:72])[CH2:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[C@H:44]([O:69][CH3:70])[C@@H:45]([CH3:68])[C:46](=[O:67])[NH:47][C@H:48]([C:56]1[O:57][C:58]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[N:59][N:60]=1)[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:38])[CH3:33])=[O:31])[CH:27]([CH3:29])[CH3:28])=[O:24])[CH:20]([CH3:22])[CH3:21])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:77])[C@H:19]([C:23]([NH:25][C@H:26]([C:30]([N:32]([C@@H:34]([C@@H:73]([CH3:76])[CH2:74][CH3:75])[C@H:35]([O:71][CH3:72])[CH2:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[C@H:44]([O:69][CH3:70])[C@@H:45]([CH3:68])[C:46](=[O:67])[NH:47][C@H:48]([C:56]1[O:57][C:58]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[N:59][N:60]=1)[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:38])[CH3:33])=[O:31])[CH:27]([CH3:29])[CH3:28])=[O:24])[CH:20]([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 86678419HCID 86678419, compound2×

Product 1

HCID 86678418HCID 86678418, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

15 mg (14 μmol) of N-(6-{[(benzyloxy)carbonyl]amino}hexyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide (Intermediate 234) were taken up in 3 ml of methanol, and 1.8 mg of palladium on charcoal (5%) were added. The reaction mixture was subsequently hydrogenated under standard hydrogen pressure at RT for 2 h. The catalyst was then filtered off and the solvent was removed under reduced pressure. The residue was lyophilized from 1:1 acetonitrile/water. 11 mg (86% of theory) of the title compound were obtained as a foam.

Workup

  1. customat RT
  2. customfor 2 h
  3. filtrationThe catalyst was then filtered off
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dd271bf577624fc3a064b5067f2d5775
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

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