Methylhydrazine → HCID 18610548, compound

HRID 256006Notes

Reaction equation

HRID 256006 reaction equation
CNN.[O:4]=[C:5]1[C@@H:11]([N:12]2C(=O)C3=CC=CC=C3C2=O)[CH2:10][S:9][CH2:8][C@@H:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:6]1[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>C(Cl)Cl>[NH2:12][C@H:11]1[CH2:10][S:9][CH2:8][C@@H:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:6]([CH2:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[C:5]1=[O:4]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 18610531HCID 18610531, compound

Product 1

HCID 18610548HCID 18610548, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.7 ml of methylhydrazine was added to a solution containing 1.65 g of t-butyl α-[5-oxo-3(R)-phenyl-6(R)-phthalimidoperhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (f) above] dissolved in 20 ml of methylene chloride, and the mixture was allowed to stand at room temperature for 2 hours. The solvent and excess methylhydrazine were then distilled off, and the residue was dissolved in 10 ml of methylene chloride and 1 ml of methanol. The resulting solution was allowed to stand overnight at room temperature, after which the solvent was removed by distillation. A small amount of methylene chloride was added to the residue, and the precipitate was filtered off. The filtrate was subjected to silica gel column chromatography eluted with a 1:20 by volume mixture of methanol and methylene chloride, to give 1.1 g of the title compound as an amorphous substance.

Workup

  1. distillationThe solvent and excess methylhydrazine were then distilled off
  2. dissolutionthe residue was dissolved in 10 ml of methylene chloride
  3. waitto stand overnight at room temperature
  4. customafter which the solvent was removed by distillation
  5. additionA small amount of methylene chloride was added to the residue
  6. filtrationthe precipitate was filtered off
  7. washeluted with a 1:20 by volume mixture of methanol and methylene chloride

Sources & evidence

ORD record
ord-be970856130f4a8fb5d26eb3e3b37035
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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