HCID 86762551, compound → HCID 86762550, compound

HRID 2207261Notes

Reaction equation

HRID 2207261 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:12]1[CH:23]=[CH:22][C:15]([C:16]([O:18][CH2:19][CH2:20][CH3:21])=[O:17])=[CH:14][CH:13]=1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[CH2:19]([O:18][C:16]([CH:15]1[CH2:22][CH2:23][CH:12]([CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:10][OH:11])[CH2:13][CH2:14]1)=[O:17])[CH2:20][CH3:21]

Participants

3

Reactant 1

HCID 86762551HCID 86762551, compound

Product 1

HCID 86762550HCID 86762550, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Propyl 4-(1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-benzoate (3) (5.35 g, 16.5 mmol) was dissolved in MeOH (150 mL). Argon was bubbled for 20 minutes. 5% Rh/C (1 g) was charged to the solution and argon was bubbled for another 10 minutes. The reaction mixture was stirred at 60 psi hydrogen pressure for 16 hours then at 100 psi for 7 days. Another portion of 10% Rh/C 1% Pd/C (1.2 g) was added. The reaction mixture was stirred at 100 psi hydrogen pressure for another 7 days after which LC/MS analysis indicated complete hydrogenation of the aromatic ring. The reaction mixture was filtered through a celite bed and rinsed with MeOH. The filtrate was concentrated under vacuum to dryness. The residue was filtered through a silica gel bed and eluted with EtOAc/Hexanes (20˜ 40%) to give 4.9 g (89.9% yield) of the pure 1-4.

Workup

  1. customArgon was bubbled for 20 minutes
  2. addition5% Rh/C (1 g) was charged to the solution and argon
  3. customwas bubbled for another 10 minutes
  4. waitat 100 psi for 7 days
  5. additionAnother portion of 10% Rh/C 1% Pd/C (1.2 g) was added
  6. stirringThe reaction mixture was stirred at 100 psi hydrogen pressure for another 7 days after which LC/MS analysis
  7. filtrationThe reaction mixture was filtered through a celite bed
  8. washrinsed with MeOH
  9. concentrationThe filtrate was concentrated under vacuum to dryness
  10. filtrationThe residue was filtered through a silica gel bed
  11. washeluted with EtOAc/Hexanes (20˜ 40%)
  12. customto give 4.9 g (89.9% yield) of the pure 1-4

Sources & evidence

ORD record
ord-58d058662526462686975edd6945df1c
Source dataset
uspto-grants-2016_06
Patent number
US09376423B2

Reaction notes

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