Acetic Acid → HCID 66597345, compound

HRID 1518617Notes

Reaction equation

HRID 1518617 reaction equation
[N:1]([CH2:4][C@@H:5]([C:7]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11](=[O:25])[NH:12]2)[OH:6])=[N+]=[N-].[C:26]([OH:29])(=[O:28])[CH3:27]>[OH-].[Pd+2].[OH-].[C]>[C:26]([OH:29])(=[O:28])[CH3:27].[NH2:1][CH2:4][C@@H:5]([C:7]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11](=[O:25])[NH:12]2)[OH:6]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 58505170(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one

Product 1

HCID 66597345HCID 66597345, compound

Reagents, catalysts & solvents 1

HCID 178502593HCID 178502593, compoundCatalyst

Procedure

5-((R)-2-Azido-1-hyroxyethyl)-8-benzyloxy-1H-quinolin-2-one (16.8 g, 49.9 mol) was suspended in acetic acid (50 mL), a catalytic amount of palladium hydroxide-carbon was added thereto, and the solution was stirred under a hydrogen atmosphere overnight. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. To the residue were added methanol (100 mL) and ethyl acetate (100 mL), and the mixture was stirred. The precipitate was collected by filtration and dried to obtain 5-((R)-2-amino-1-hyroxyethyl)-8-hydroxy-1H-quinolin-2-one acetate (12.5 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue were added methanol (100 mL) and ethyl acetate (100 mL)
  4. stirringthe mixture was stirred
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-2a40e6429aeb40aa9905f622e7ded49f
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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