HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

(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 351651
Notes
Print preview

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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 AcidSolvent
HCID 887
Methanol
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06743800B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes