Hydrazinecarboxylic acid, ethyl ester → HCID 178473583, compound

HRID 1951632Notes

Reaction equation

HRID 1951632 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-c34bbf1c72174a449e3bfb283cc76b22
Source dataset
uspto-grants-2013_03
Patent number
US08404732B2

Reaction notes

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