L-Glutamic Acid → HCID 178484385, compound

HRID 1427066Notes

Reaction equation

HRID 1427066 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]([NH:5][C:6](=[NH:8])[NH2:7])=[NH:4].[NH2:10][C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][CH2:13][C:14]([OH:16])=[O:15]>CO>[NH2:10][C@@H:11]([CH2:12][CH2:13][C:14]([O-:16])=[O:15])[C:17]([O-:19])=[O:18].[CH3:1][N:2]([C:3]([NH:5][C:6](=[NH:7])[NH3+:8])=[NH:4])[CH3:9].[CH3:1][N:2]([C:3]([NH:5][C:6](=[NH:7])[NH3+:8])=[NH:4])[CH3:9]

Participants

4

Reactant 2

HCID 33032L-Glutamic AcidHCID 178484382HCID 178484382, compound

Product 1

HCID 178484385HCID 178484385, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of N,N-dimethylimidodicarbonimidic diamide (1.00 g, 7.74 mmol) in methanol (40 mL) is treated with a solution of L-glutamic acid (0.570 g, 3.87 mmol) in methanol (40 mL) at RT under N2. The mixture is stirred at RT for ½ hr. The methanol is evaporated and the remaining oil is triturated with CH3CN to give a white solid. The solid is dried at RT under hi-vac for 3 hrs, then stirred in CH3CN (50 ml) at RT for 2 hrs. The solid is collected by filtration and dried under hi-vac at RT for 1 hr to give 1.3 g of bis[{[(dimethylamino)(imino)methyl]amino}-(imino)methanaminium] (2S)-2-aminopentanedioate as a white solid. 1H NMR (300 MHz, MeOD) d 1.88 (m, 1H) 2.06 (m, 2H) 2.30 (m, 2H) 3.05 (s, 12H) 4.91 (s, 14H); MS (ESI−) for C5H9NO4 m/z 146 (M−H)−. MS (ESI+) for C4H11N5 m/z 130 (M+H)+. Anal Calcd for C13H3N11O4 plus 0.75% H2O: C, 38.22; H, 7.73; N, 37.71. Found: C, 38.57; H, 7.65; N, 36.73.

Workup

  1. customThe methanol is evaporated
  2. customthe remaining oil is triturated with CH3CN
  3. customto give a white solid
  4. customThe solid is dried at RT under hi-vac for 3 hrs
  5. stirringstirred in CH3CN (50 ml) at RT for 2 hrs
  6. filtrationThe solid is collected by filtration
  7. customdried under hi-vac at RT for 1 hr

Sources & evidence

ORD record
ord-c0e37b23db5b4b77bf6acc35fc23fb6b
Source dataset
uspto-grants-2015_01
Patent number
US08933124B2

Reaction notes

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