HCID 86694562, compound → HCID 86694561, compound

HRID 1426391Notes

Reaction equation

HRID 1426391 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:25]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:10][CH2:11][CH:12]1[O:14][CH:13]1[C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:25]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:10][CH2:11][CH:12]([OH:14])[CH2:13][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86694562HCID 86694562, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86694561HCID 86694561, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[3-((3R,4S)-3-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(dimethyl)silyl]oxy}-5-phenoxypentyl)oxiran-2-yl]benzoate from step D (410 mg, 0.7 mM) in 15 ml of methanol was added 100 mg of palladium on carbon (10%) and the suspension was set under 40 PSI of hydrogen gas and shaken for 2 h on the Parr shaker. The catalyst was filtered and the filtrate concentrated under reduced pressure to afford 378 mg of the title compound which was directly used for next step. LC-MS: m/z (ES) 488.21 (M-Boc+1).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7815c4a24357448a9e6f5ec5174d3324
Source dataset
uspto-grants-2015_01
Patent number
US08933102B2

Reaction notes

Loading…