HCID 178453881, compound → HCID 178453882, compound

HRID 29763Notes

Reaction equation

HRID 29763 reaction equation
[C:1]([O:5][C:6](=[O:34])[C:7](=[CH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:21]1)[CH2:8][C:9]([O:11]CC1C=CC=CC=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:34])[CH:7]([CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:21]1)[CH2:8][C:9]([OH:11])=[O:10])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 178453881HCID 178453881, compound

Product 1

HCID 178453882HCID 178453882, compoundYield 110.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of trans-2-(4-tert-Butoxycarbonylamino-cyclohexylmethylene)-succinic acid 4-benzyl ester 1-tert-butyl ester (243 mg, 0.51 mmol) and palladium (5% on charcoal) in ethanol (15 mL) was hydrogenated at 4 bar for 3 h. The catalyst was removed from the reaction mixture by filtration. The catalyst was washed with ethanol and the solution was concentrated under reduced pressure to give crude trans-2-(4-tert-Butoxycarbonylamino-cyclohexylmethyl)-succinic acid 1-tert-butyl ester (217 mg, >100%).

Workup

  1. customThe catalyst was removed from the reaction mixture by filtration
  2. washThe catalyst was washed with ethanol
  3. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45ec8ba67c6e4ef2a7d93f8daab3660c
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Reaction notes

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