HCID 89668414, compound → HCID 131736687, compound

HRID 1482230Notes

Reaction equation

HRID 1482230 reaction equation
[NH:1]([C:46]([O:48][CH2:49][CH:50]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:56]2[C:51]1=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:47])[C@H:2]([C:14]([N:16]([CH3:45])[C@H:17]([C:25]([N:27]([CH3:44])[C@H:28]([C:36]([NH:38][C@H:39]([C:41]([OH:43])=[O:42])[CH3:40])=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:3][C:4](=[O:13])[O:5]CC1C=CC=CC=1.[H][H]>[Pd].CO>[NH:1]([C:46]([O:48][CH2:49][CH:50]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:56]2[C:51]1=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:47])[C@H:2]([C:14]([N:16]([CH3:45])[C@H:17]([C:25]([N:27]([CH3:44])[C@H:28]([C:36]([NH:38][C@H:39]([C:41]([OH:43])=[O:42])[CH3:40])=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:15])[CH2:3][C:4](=[O:5])[OH:13]

Participants

5

Reactant 2

HCID 89668414HCID 89668414, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131736687HCID 131736687, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Fmoc-Asp(OBn)-MePhe-MePhe-Ala-pip (Compound SP457) (8.06 g, 8.90 mmol) and 20% palladium on active carbon (1.61 g, 3.0 mmol) were added to methanol (50 ml) under a nitrogen atmosphere, the atmosphere in the reaction vessel was replaced with hydrogen gas, and the mixture was stirred at room temperature for 5 hours. The reaction solution was filtered through celite, and the organic layer was concentrated under reduced pressure to afford Fmoc-Asp-MePhe-MePhe-Ala-pip (Compound SP458) (4.79 g, 66%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a58e18d5a5494ba5b3e5387513f13209
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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