Hydrazine hydrate (1:1) → HCID 178465585, compound

HRID 418262Notes

Reaction equation

HRID 418262 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].O.[NH2:18][NH2:19]>CO.O.C(O)(=O)C.O1CCCC1>[N:18](=[C:14]([C:11]1[NH:12][CH:13]=[C:9]([C@@H:2]([OH:1])[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6])[N:10]=1)[CH3:15])[NH2:19]

Participants

7

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178467425HCID 178467425, compound

Product 1

HCID 178465585HCID 178465585, compound

Reagents, catalysts & solvents 4

HCID 176Acetic 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 (THI, prepared according to Halweg, K. M. and Büchi, G., J. Org. Chem. 50:1134-1136 (1985)) (148 mg, 0.64 mmol) was suspended in methanol (3 ml) and water (1 ml). Hydrazine hydrate (35 mg, 0.7 mmol, 1.2 eq.) and acetic acid (one drop) were added, and the suspension was stirred at 50° C. for 6 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: 90 mg (58%).

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-15da2ebb0847499bb441970508fc4d58
Source dataset
uspto-grants-2012_01
Patent number
US08093267B2

Reaction notes

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