Hydrazine hydrate (1:1) → HCID 18610546, compound

HRID 256082Notes

Reaction equation

HRID 256082 reaction equation
O.NN.[O:4]=[C:5]1[C@@H:11]([N:12]2C(=O)C3=CC=CC=C3C2=O)[CH2:10][S:9][CH:8]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH2:7][N:6]1[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CO>[NH2:12][C@H:11]1[CH2:10][S:9][CH:8]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH2:7][N:6]([CH2:28][C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C:5]1=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18610532t-butyl alpha-[5-oxo-6(R)-phthalimido-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate

Product 1

HCID 18610546HCID 18610546, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7 ml of hydrazine hydrate were added to a suspension of 34.1 g of t-butyl α-[5-oxo-6(R)-phthalimido-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (f) above] in 340 ml of methanol, to form a homogeneous solution. This was left standing for 2 days at room temperature, and then the resulting precipitate was filtered off. The filtrate was condensed by evaporation under reduced pressure, and then 200 ml of methylene chloride were added to the residue. The mixture was stirred and insoluble matter was filtered off. The filtrate was washed with water and dried over anhydrous magnesium sulfate, after which the solvent was evaporated off. The residue was crystallized by adding diisopropyl ether containing a small amount of hexane, to yield 22.3 g of the title compound, melting at 81°-82° C.

Workup

  1. customto form a homogeneous solution
  2. waitThis was left
  3. filtrationthe resulting precipitate was filtered off
  4. customcondensed
  5. customby evaporation under reduced pressure
  6. addition200 ml of methylene chloride were added to the residue
  7. filtrationinsoluble matter was filtered off
  8. washThe filtrate was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customafter which the solvent was evaporated off
  11. customThe residue was crystallized
  12. additionby adding diisopropyl ether containing a small amount of hexane

Sources & evidence

ORD record
ord-2d0a6f9219e74d87acfce99b24d7dfc0
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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