HCID 86660915, compound → HCID 58046611, compound

HRID 1751115Notes

Reaction equation

HRID 1751115 reaction equation
[C:1]([O:5][C:6](=[O:41])[C@@H:7]([N:14]1[C:18](=[O:19])[C:17]2([CH2:24][CH2:23][N:22](C(OCC3C=CC=CC=3)=O)[CH2:21][CH2:20]2)[N:16]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd]>[O:19]=[C:18]1[C:17]2([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[N:16]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:15][N:14]1[C@@H:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:41]

Participants

5

Reactant 1

HCID 86660915HCID 86660915, compound

Product 1

HCID 58046611HCID 58046611, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-benzyl 3-(2-tert-butoxy-2-oxo-1-phenylethyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (1.88 g, 3.39 mmol, 1 equiv) in a mixture of ethyl acetate and ethanol was charged with 10% palladium on carbon (1 g, 20%/wt) and the resulting mixture was hydrogenated at atmospheric pressure for 2 h. The reaction was filtered over Celite and the filtrate was concentrated and dried in vacuo to afford the title compound as a dark grey foam (1.24 g, 93%); MS for C25H31N3O3 m/z 422.24 (M+H)+.

Workup

  1. filtrationThe reaction was filtered over Celite
  2. concentrationthe filtrate was concentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-bb6288cf1c6e4de3964a6642262ec3a7
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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