HCID 131728266, compound → HCID 69176521, compound

HRID 499704Notes

Reaction equation

HRID 499704 reaction equation
[CH3:1][O:2][C:3](=[O:37])[NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:15](=[O:36])[CH2:16][C:17]([CH3:35])([CH3:34])[CH2:18][C@H:19]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:20]([OH:25])[CH2:21][N:22]=[N+]=[N-])[CH2:6]1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:37])[NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:15](=[O:36])[CH2:16][C:17]([CH3:35])([CH3:34])[CH2:18][C@H:19]([NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C@@H:20]([OH:25])[CH2:21][NH2:22])[CH2:6]1

Participants

4

Reactant 1

HCID 131728266HCID 131728266, compound

Product 1

HCID 69176521HCID 69176521, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.37 g of [1-(7-azido-5(S)-tert-butoxycarbonylamino-6(S)-hydroxy-3,3-dimethyl-heptanoyl)-1,2,3,4-tetrahydro-quinolin-3(R,S)-yl]-carbamic acid methyl ester and 75 mg of 10% Pd/C in 15 ml of methanol is hydrogenated at room temperature for 2 hours. The solid is removed by filtration over Hyflo® and the solution is concentrated. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60 F). Rf=0.12 (200:40:1 dichloromethane-methanol-25% conc. ammonia); Rt=3.43 (gradient I).

Workup

  1. customThe solid is removed by filtration over Hyflo®
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-c1d9c9e64a124661b17452c4fce3ed9e
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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