HCID 86613532, compound → HCID 59588942, compound

HRID 2237733Notes

Reaction equation

HRID 2237733 reaction equation
[N:1]([CH2:4][C@@H:5]([C@@H:7]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:8][C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH:15]=1)[CH:10]([CH3:12])[CH3:11])[OH:6])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([C@@H:7]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:8][C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH:15]=1)[CH:10]([CH3:12])[CH3:11])[OH:6]

Participants

4

Reactant 1

HCID 86613532HCID 86613532, compound

Product 1

HCID 59588942HCID 59588942, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The solution of 0.185 g of tert-butyl {1(S)-(2-azido-1(S)-hydroxyethyl)-3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate in 6 ml of methanol is hydrogenated in the presence of 0.037 g of 10% Pd/C over 2 hours. The reaction mixture is clarified by filtration and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly greyish oil. Rf=0.08 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=15.47 (gradient II).

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-743b6da1c8ab473d879fdba9169889b6
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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