Sodium Carbonate → 2-Amino-6-methyl-6-nitroheptanoic acid

HRID 432986Notes

Reaction equation

HRID 432986 reaction equation
[CH3:1][C:2]([N+:14]([O-:16])=[O:15])([CH3:13])[CH2:3][CH2:4][CH2:5][CH:6]1[NH:10]C(=O)N[C:7]1=[O:12].[OH-].[Na+].[OH-].[K+].C(=O)([O-])[O-:22].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[OH-].[Ca+2].[OH-].[OH-].[Ba+2].[OH-]>>[NH2:10][CH:6]([CH2:5][CH2:4][CH2:3][C:2]([CH3:1])([N+:14]([O-:16])=[O:15])[CH3:13])[C:7]([OH:12])=[O:22]

Participants

8

Reactant 7

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 6093208Calcium HydroxideHCID 6093286Barium hydroxideHCID 99427025-(4-Methyl-4-nitropentyl)hydantoin2×

Product 1

HCID 219723372-Amino-6-methyl-6-nitroheptanoic acid

Procedure

5-(4-Methyl-4-nitropentyl)hydantoin is hydrolyzed with alkali to give 2-amino-6-methyl-6-nitroheptanoic acid (see JP-A-11-140076). For example, 5-(4-methyl-4-nitropentyl)hydantoin is hydrolyzed in an aqueous solution preferably in the presence of 1-3 equivalents of alkali, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, calcium hydroxide, barium hydroxide and the like, relative to 5-(4-methyl-4-nitropentyl)hydantoin generally at 20-200° C., preferably 100-150° C. The reaction mixture is concentrated to dryness to give 2-amino-6-methyl-6-nitroheptanoic acid. The obtained 2-amino-6-methyl-6-nitroheptanoic acid can be isolated and/or purified by a conventional method, such as crystallization, chromatography and the like, but generally, can be used in the next step without isolation and/or purification.

Workup

  1. customgenerally at 20-200° C.
  2. custompreferably 100-150° C
  3. concentrationThe reaction mixture is concentrated to dryness

Sources & evidence

ORD record
ord-5ffe684c56f047b38ec1e138f66e8a4b
Source dataset
uspto-grants-2003_12
Patent number
US06664412B2

Reaction notes

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