(2s)-2-Benzyloxycarbonylamino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)-purin-9-yl)-propionic acid tert-butyl ester → (2s)-2-Amino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)purin-9-yl)-propionic acid tert-butyl ester

HRID 351651Notes

Reaction equation

HRID 351651 reaction equation
[C:1]([O:5][C:6](=[O:45])[C@@H:7]([NH:34]C(OCC1C=CC=CC=1)=O)[CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:33]=[CH:32][C:31]3[CH2:30][CH2:29][CH2:28][NH:27][C:26]=3[N:25]=2)[CH2:20][CH2:19]1)([CH3:4])([CH3:3])[CH3:2]>CO.C(O)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:45])[C@@H:7]([NH2:34])[CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:33]=[CH:32][C:31]3[CH2:30][CH2:29][CH2:28][NH:27][C:26]=3[N:25]=2)[CH2:20][CH2:19]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 11422135(2s)-2-Benzyloxycarbonylamino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)-purin-9-yl)-propionic acid tert-butyl ester

Product 1

HCID 11352047(2s)-2-Amino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)purin-9-yl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

878 mg of the compound of example 1, step d) were dissolved in 50 ml of methanol and 0.4 ml of acetic acid. Under a nitrogen atmosphere 350 mg of 10% palladium on charcoal were carefully added, and hydrogenation was performed under shaking of the reaction vessel. After 5 hours the reaction was complete. The solvents were removed after filtration of the catalyst Yield: 680 mg of a resinous product. MS (ES+): m/e=479.3 (M+H)+.

Workup

  1. customThe solvents were removed
  2. filtrationafter filtration of the catalyst Yield: 680 mg of a resinous product

Sources & evidence

ORD record
ord-6f2cd4ba41d14a868bf0137ef0a39349
Source dataset
uspto-grants-2004_06
Patent number
US06743800B1

Reaction notes

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