Ammonia → 3-(Carbamoylmethyl)-5-methylhexanoic acid

HRID 1780228Notes

Reaction equation

HRID 1780228 reaction equation
[CH2:1]([CH:5]1[CH2:11][C:10](=[O:12])[O:9][C:7](=[O:8])[CH2:6]1)[CH:2]([CH3:4])[CH3:3].[NH3:13]>>[C:7]([CH2:6][CH:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:11][C:10]([OH:9])=[O:12])(=[O:8])[NH2:13]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 11480690Dihydro-4-(2-methylpropyl)-2H-pyran-2,6(3H)-dione

Product 1

HCID 108670833-(Carbamoylmethyl)-5-methylhexanoic acid

Procedure

In another step of the method, 3-isobutylglutaric acid anhydride is reacted with ammonia to form (±)-3-(carbamoylmethyl)-5-methylhexanoic acid. In this step, the cyclic anhydride is opened and one of the carbonyl groups is converted to an amide. (±)-3-(carbamoyl methyl)-5-methylhexanoic acid can be recrystallized from a number of solvents including ethyl acetate, water, chloroform and 2-butanone.

Sources & evidence

ORD record
ord-56591bc11fc544b885a5aa59ae691542
Source dataset
uspto-grants-1997_05
Patent number
US05629447

Reaction notes

Loading…