Hydrochloric Acid → (S)-2-amino-6-methyl-6-nitroheptanoic acid

HRID 858962Notes

Reaction equation

HRID 858962 reaction equation
C([NH:4][CH:5]([CH2:9][CH2:10][CH2:11][C:12]([CH3:17])([N+:14]([O-:16])=[O:15])[CH3:13])[C:6]([OH:8])=[O:7])(=O)C.[OH-].[Na+].Cl>O.[Co](Cl)Cl>[NH2:4][C@@H:5]([CH2:9][CH2:10][CH2:11][C:12]([CH3:17])([N+:14]([O-:16])=[O:15])[CH3:13])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98562682-Acetylamino-6-methyl-6-nitroheptanoic acid

Product 1

HCID 9834264(S)-2-amino-6-methyl-6-nitroheptanoic acid

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 962WaterSolvent

Procedure

2-Acetylamino-6-methyl-6-nitroheptanoic acid (49.5 g, 200 mmol) was dissolved in water (246 ml) and 30% sodium hydroxide was added to adjust its pH to 8.87. L-Acylase (4.95 g) and anhydrous cobalt chloride (0.27 g) were added to adjust its pH to 9 and the mixture was stirred overnight at room temperature. Concentrated hydrochloric acid was added to adjust its pH to 1.5 and the mixture was ice-cooled. The precipitated crystals were separated by filtration and the filtrate was washed twice with a mixture (250 ml) of toluene-isopropyl alcohol (1:1) and the aqueous layer was concentrated under reduced pressure. Methanol (100 ml) was added for concentration and methanol (100 ml) was further added for concentration. As a result, the objective compound was obtained (20.5 g).

Workup

  1. temperaturecooled
  2. customThe precipitated crystals were separated by filtration
  3. washthe filtrate was washed twice with a mixture (250 ml) of toluene-isopropyl alcohol (1:1)
  4. concentrationthe aqueous layer was concentrated under reduced pressure
  5. additionMethanol (100 ml) was added for concentration and methanol (100 ml)
  6. additionwas further added for concentration
  7. customAs a result, the objective compound was obtained (20.5 g)

Sources & evidence

ORD record
ord-fd56a4dc4dbf49d4be2dea7aebc4b318
Source dataset
uspto-grants-2006_12
Patent number
US07148371B2

Reaction notes

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