HCID 70235472, compound → HCID 53670982, compound

HRID 1387470Notes

Reaction equation

HRID 1387470 reaction equation
[C:1]([O:5][C:6](=[O:36])[CH2:7][C@H:8]([N:20](CC1C=CC=CC=1)[C@@H](C1C=CC=CC=1)C)[C:9]1[CH:18]=[C:17]2[C:12]([O:13][CH2:14][C:15](=[O:19])[NH:16]2)=[N:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.O.CC(O)=O>[C:1]([O:5][C:6](=[O:36])[CH2:7][C@H:8]([NH2:20])[C:9]1[CH:18]=[C:17]2[C:12]([O:13][CH2:14][C:15](=[O:19])[NH:16]2)=[N:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 70235472HCID 70235472, 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-52a102d4a2974155a989920ef90a594c
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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