Hydrazinecarboxylic acid, ethyl ester → HCID 178473583, compound

HRID 418265Notes

Reaction equation

HRID 418265 reaction equation
[OH:1][C@H:2]([C:9]1[N:10]=[C:11]([C:14](=O)[CH3:15])[NH:12][CH:13]=1)[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[NH:18][NH2:19]>CO.O.Cl>[OH:1][C@H:2]([C:9]1[N:10]=[C:11](/[C:14](=[N:19]/[NH:18][C:17]([O:21][CH2:22][CH3:23])=[O:20])/[CH3:15])[NH:12][CH:13]=1)[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6]

Participants

6

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 178467425HCID 178467425, compound

Product 1

HCID 178473583HCID 178473583, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1-[4-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-1H-imidazol-2-yl]-ethanone (150 mg, 0.65 mmol) was suspended in methanol (3 ml) and water (1 ml). Ethyl carbazate (78 mg, 0.75 mmol, 1.2 eq.) and hydrochloric acid (one drop, 12 N) were added, and the suspension was stirred at 50° C. for 18 hours. LCMS analysis indicated the formation of the product and the absence of starting material. The reaction mixture was cooled to room temperature, concentrated in vacuo, and diluted with acetone. The resulting white precipitate was collected and washed with acetone to yield the product, one apparent isomer, as a white solid: 96 mg (47%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additiondiluted with acetone
  4. customThe resulting white precipitate was collected
  5. washwashed with acetone
  6. customto yield the product, one apparent isomer

Sources & evidence

ORD record
ord-9a944ef81a984f84998290b0c33dd3c0
Source dataset
uspto-grants-2012_01
Patent number
US08093267B2

Reaction notes

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