Formic Acid → HCID 86598329, compound

HRID 1393386Notes

Reaction equation

HRID 1393386 reaction equation
C(O)=O.[CH2:4]([O:6][C:7](=[O:54])[C@H:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][C:29]=3[N:33]([CH2:44][CH2:45][O:46]CC3C=CC=CC=3)[CH2:34][CH2:35][O:36]CC3C=CC=CC=3)[CH:24]=2)[CH:18]=1)[NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[CH3:5]>[OH-].[Pd+2].[OH-].C(O)C>[CH2:4]([O:6][C:7](=[O:54])[C@H:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][C:29]=3[N:33]([CH2:44][CH2:45][OH:46])[CH2:34][CH2:35][OH:36])[CH:24]=2)[CH:18]=1)[NH:9][C:10](=[O:15])[C:11]([F:13])([F:14])[F:12])[CH3:5]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 86598328HCID 86598328, compound

Product 1

HCID 86598329HCID 86598329, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Ethanol (10 ml), formic acid (1.94 ml, 52 mmol) and 20% palladium hydroxide (145 mg) were added to 3-[5-bis[2-(benzyloxy)ethyl]amino-naphth-2-yl]-N-trifluoroacetyl-L-phenylalanine ethyl ester (739 mg, 1.03 mmol) and the mixture was heated under reflux for 3 days. After the mixture was cooled to room temperature, the catalyst was filtered off and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/chloroform=1 and 2) to give 3-[5-bis[2-(hydroxy)ethyl]amino-naphth-2-yl]-N-trifluoroacetyl-L-phenylalanine ethyl ester (395 mg, 71%) as a dark yellow foam.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 days
  3. filtrationthe catalyst was filtered off
  4. distillationthe solvent of the filtrate was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate/chloroform=1 and 2)

Sources & evidence

ORD record
ord-5d95059f4aa94a5995128ba79a1119e6
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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