HCID 86705260, compound → HCID 86705261, compound

HRID 879211Notes

Reaction equation

HRID 879211 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[CH2:12][C@H:11]([CH3:24])[C@H:10]1[O:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[NH2:21][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[C@@H:13]1[CH2:12][C@H:11]([CH3:24])[C@@H:10]([O:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:14]1

Participants

4

Reactant 1

HCID 86705260HCID 86705260, compound

Product 1

HCID 86705261HCID 86705261, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (+/−)-methyl 3-((1R,2R,6S)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyloxy)propanoate (1.0 equiv.) in degassed EtOH (0.07 M) was added Pd/C (0.3 equiv.). The mixture was purged with H2, and allowed to stir under H2 overnight at RT. The reaction was filtered through a pad of celite and the cake was washed with MeOH. The organics were concentrated and purified by ISCO SiO2 chromatography to yield (+/−)-methyl 3-((1R,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyloxy)propanoate in 100% yield. LC/MS (m/z)=408.2 (MH+), Rt=0.62 min.

Workup

  1. customThe mixture was purged with H2
  2. filtrationThe reaction was filtered through a pad of celite
  3. washthe cake was washed with MeOH
  4. concentrationThe organics were concentrated
  5. custompurified by ISCO SiO2 chromatography

Sources & evidence

ORD record
ord-77abbd80ce9f4daea6d45a1e6b3df42a
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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