Methylhydrazine → HCID 20164914, compound

HRID 256044Notes

Reaction equation

HRID 256044 reaction equation
[C:1]([O:5][C:6](=[O:37])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([N:16]2C(=O)C3=CC=CC=C3C2=O)[CH2:12][S:11][CH:10]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CNN>C(Cl)Cl.CO>[NH2:16][CH:13]1[CH2:12][S:11][CH:10]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[CH2:9][N:8]([CH2:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:37])[C:14]1=[O:15]

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 20164974HCID 20164974, compound

Product 1

HCID 20164914HCID 20164914, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.5 g of t-butyl[2-(1-naphthyl)-5-oxo-6-phthalimidoperhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (f) above] in a mixture of 20 ml of methylene chloride and 2 ml of methanol was added 0.77 ml of methylhydrazine, and the reaction mixture was allowed to stand for 2 days at room temperature. The reaction mixture was then concentrated by evaporation under reduced pressure, 15 ml of methylene chloride were added to the residue and the mixture was stirred. The resulting precipitate was filtered off and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography using a 1:20 by volume mixture of methanol and ethyl acetate as eluent, to give 1.92 g of the title compound as an amorphous solid.

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure, 15 ml of methylene chloride
  2. additionwere added to the residue
  3. filtrationThe resulting precipitate was filtered off
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. additionby volume mixture of methanol and ethyl acetate as eluent

Sources & evidence

ORD record
ord-e1eddabbda7f4162bd46df320498faed
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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