Hydrazine hydrate (1:1) → HCID 18394513, compound

HRID 1602081Notes

Reaction equation

HRID 1602081 reaction equation
O.NN.[CH3:4][NH:5][C:6](=[O:42])[C@H:7]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[NH:8][C:9](=[O:34])[C@H:10]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:11][S:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]1C(=O)C2=CC=CC=C2C1=O)(=[O:14])=[O:13]>C(O)C.C(Cl)(Cl)Cl.O>[CH3:4][NH:5][C:6](=[O:42])[C@H:7]([CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[NH:8][C:9](=[O:34])[C@H:10]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:11][S:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])(=[O:14])=[O:13]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67606853HCID 67606853, compound

Product 1

HCID 18394513HCID 18394513, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Hydrazine hydrate (56%, 18.2 ml) was added to a solution of example 17 (7.1 g) in ethanol (120 ml) and the mixture was heated at reflux for 30 min. The mixture was then cooled to RT and diluted with ethanol (300 ml), chloroform (100 ml) and water (200 ml). The layers were separated and the organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was then purified by flash column chromatography, eluting with 0-10% methanol in chloroform containing 2.5% triethylamine, to give the title compound (5.39 g, 99%) as a colourless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 min
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was then purified by flash column chromatography
  7. washeluting with 0-10% methanol in chloroform containing 2.5% triethylamine

Sources & evidence

ORD record
ord-d15d6a99e99a4cf7a7d6bdb226918dab
Source dataset
uspto-grants-1999_11
Patent number
US05981491

Reaction notes

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