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

HRID 1169857Notes

Reaction equation

HRID 1169857 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-0b57dedbcf14484d9d51ab7434bfa7ad
Source dataset
uspto-grants-2010_11
Patent number
US07825150B2

Reaction notes

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