HCID 20681537, compound → HCID 70203736, compound

HRID 651794Notes

Reaction equation

HRID 651794 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:19]([NH:21][N:22]1[C:26](=[O:27])[C:25]2([CH2:32][CH2:31][N:30](C(OCC3C=CC=CC=3)=O)[CH2:29][CH2:28]2)[NH:24][C:23]1=[O:43])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:19]([NH:21][N:22]1[C:26](=[O:27])[C:25]2([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[NH:24][C:23]1=[O:43])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 20681537HCID 20681537, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70203736HCID 70203736, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.01 g of benzyl 3-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvaleramido]-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate in 15 ml of methanol was treated with 0.432 g of 10% palladium-on-charcoal catalyst. The mixture was shaken in a hydrogen atmosphere for 18 hours. The catalyst was filtered off and the methanol evaporated. The residue was triturated with ether and there was obtained 0.81 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methyl-N-[2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl]valeramide in the form of a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe methanol evaporated
  3. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-09582ad53d6f4875ada2fc4d9aeb2feb
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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