Methanol → HCID 14799075, compound

HRID 2248030Notes

Reaction equation

HRID 2248030 reaction equation
C(O)(=O)/C=C/C(O)=O.[NH2:9][C:10]([CH3:21])([CH3:20])[C:11]([NH:13][CH2:14][CH2:15][O:16][N+:17]([O-:19])=[O:18])=[O:12].CO.O.[O-:25][C:26]#[N:27].[K+]>C(O)(=O)C>[NH2:27][C:26]([NH:9][C:10]([CH3:21])([CH3:20])[C:11]([NH:13][CH2:14][CH2:15][O:16][N+:17]([O-:19])=[O:18])=[O:12])=[O:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11378442Potassium cyanateHCID 86744964HCID 86744964, compound

Product 1

HCID 14799075HCID 14799075, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.77 g. 2-Amino-2-methyl-N-(2-nitroxyethyl)-propionic acid amide fumarate is dissolved in 7.5 ml. methanol and 2.5 ml. water and 0.81 g. potassium cyanate added thereto. The reaction mixture is stirred for 10 minutes at ambient temperature and then 0.30 g. acetic acid added thereto. After stirring overnight, the inorganic salts are precipitated out by the addition of 25 ml. ethyl acetate and filtered off with suction. The filtrate is dried over anhydrous sodium sulphate, filtered with suction and evaporated, 0.60 g. of crude product being obtained. This is triturated with diethyl ether and filtered off with suction. There is obtained 0.40 g. of the title compound, i.e. 68% of theory; m.p. 98°-100° C.

Workup

  1. stirringAfter stirring overnight
  2. customthe inorganic salts are precipitated out by the addition of 25 ml
  3. filtrationethyl acetate and filtered off with suction
  4. dry with materialThe filtrate is dried over anhydrous sodium sulphate
  5. filtrationfiltered with suction
  6. customevaporated
  7. customof crude product being obtained
  8. customThis is triturated with diethyl ether
  9. filtrationfiltered off with suction
  10. customThere is obtained 0.40 g

Sources & evidence

ORD record
ord-86c1f985c4a44a3781decde5a9905db0
Source dataset
uspto-grants-1991_08
Patent number
US05037849

Reaction notes

Loading…