2-Oxoglutaric Acid → HCID 10442822, compound

HRID 654121Notes

Reaction equation

HRID 654121 reaction equation
O=[C:2]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[C:3]([OH:5])=[O:4].Cl.[NH2:12][CH2:13][C:14]([NH2:16])=[O:15].[OH-].[Na+].O>>[C:3]([C:2]1([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[NH:16][C:14](=[O:15])[CH2:13][NH:12]1)([OH:5])=[O:4]

Participants

5

Reactant 4

HCID 512-Oxoglutaric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 2723639Glycinamide hydrochloride

Product 1

HCID 10442822HCID 10442822, compoundYield 43%

Procedure

A solution of 2-oxoglutaric acid (10 g, 0.068 mol), glycinamide hydrochloride (8.3 g, 0.075 mol) and sodium hydroxide (8.2 g, 0.205 mol) in water (120 mol) was refluxed for 4 hours. After cooling the solution was adjusted to pH 2.5 and the resulting precipitate was collected and dried under vacuum at 60° C. to afford 5.9 g (43%) of the title compound, m.p. 202°-205° C. NMR (DMSO-d6): deltaH =8.5 (s, 1H, CONH); 7.00-4.00 (b.s., 3H, NH, COOH); 3.22 and 3.18 (ABq, J=16 Hz, 2H, NHCH2CO); 2.40-1.75 (c.a., 4H, CH2CH2COOH). MS (E.I., 70 eV, 15 mA) m/z=140 (M--H2O--COOH)+, 84 C3H4N2O)+.

Workup

  1. temperatureAfter cooling the solution
  2. customthe resulting precipitate was collected
  3. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-798e2ca789cb4df18f72e831a1625a08
Source dataset
uspto-grants-1992_07
Patent number
US05130319

Reaction notes

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