Acetohydrazide → HCID 178475136, compound

HRID 418263Notes

Reaction equation

HRID 418263 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]([NH:20][NH2:21])(=[O:19])[CH3:18]>CO.O.Cl.O1CCCC1>[OH:1][C@H:2]([C:9]1[N:10]=[C:11]([C:14](=[N:21][NH:20][C:17](=[O:19])[CH3:18])[CH3:15])[NH:12][CH:13]=1)[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6]

Participants

7

Reactant 2

HCID 14039AcetohydrazideHCID 178467425HCID 178467425, compound

Product 1

HCID 178475136HCID 178475136, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1-[4-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-1H-imidazol-2-yl]-ethanone (160 mg, 0.70 mmol) was suspended in methanol (3 ml) and water (1 ml). Acetic hydrazide (56 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 48 hours. LCMS analysis indicated the formation of the product and the absence of starting material. The reaction mixture was cooled to room temperature and diluted with tetrahydrofuran. The resulting white precipitate was collected and washed with tetrahydrofuran to yield the product, a mixture of approximately 3:1 E:Z isomers, as a white solid: 129 mg (65%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe resulting white precipitate was collected
  3. washwashed with tetrahydrofuran
  4. customto yield the product
  5. additiona mixture of approximately 3:1 E

Sources & evidence

ORD record
ord-3a4c43b0c12744af887d6baefc92d073
Source dataset
uspto-grants-2012_01
Patent number
US08093267B2

Reaction notes

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