HCID 86755415, compound → HCID 53670982, compound

HRID 1108417Notes

Reaction equation

HRID 1108417 reaction equation
C([N:8]([C@@H](C1C=CC=CC=1)C)[C@H:9]([C:14]1[CH:23]=[C:22]2[C:17]([O:18][CH2:19][C:20](=[O:24])[NH:21]2)=[N:16][CH:15]=1)[CH2:10][C:11]([OH:13])=[O:12])C1C=CC=CC=1>CCO.O.CC(O)=O>[C:14]([O:13][C:11](=[O:12])[CH2:10][C@H:9]([NH2:8])[C:14]1[CH:23]=[C:22]2[C:17]([O:18][CH2:19][C:20](=[O:24])[NH:21]2)=[N:16][CH:15]=1)([CH3:23])([CH3:15])[CH3:9]

Participants

3

Reactant 1

HCID 86755415HCID 86755415, compound

Product 1

HCID 53670982HCID 53670982, compound

Reagents, catalysts & solvents 1

HCID 86584229Acetic acid ethanol waterSolvent

Procedure

A mixture of the dibenzylamine 20-6 (0.22 g, 0.44 mmol) in EtOH/H2O/AcOH (26 mL/3 mL/1.0 mL) was degassed with argon and treated with Pd(OH)2 (100 mg). The mixture was placed under 1 atm of H2. After stirring for 18 h, the mixture was diluted with EtOAc and filtered through celite. The filtrate was concentrated and the residue purified by flash chromatography (20% 20:1:1 EtOH/NH4OH/H2O-80% EtOAc) to give the tert-butyl ester 20-7 as a white solid.

Workup

  1. customwas degassed with argon
  2. additiontreated with Pd(OH)2 (100 mg)
  3. additionthe mixture was diluted with EtOAc
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified by flash chromatography (20% 20:1:1 EtOH/NH4OH/H2O-80% EtOAc)

Sources & evidence

ORD record
ord-ccc3cdb0676e47259157f43b568f9f09
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

Loading…