Hydrazine hydrate (1:1) → HCID 14301775, compound

HRID 868237Notes

Reaction equation

HRID 868237 reaction equation
O.NN.[C:4]([O:8][C:9]([C@@H:11]([NH:27][C@H:28]1[CH2:34][S:33][C@H:32]([C:35]2[S:36][CH:37]=[CH:38][CH:39]=2)[CH2:31][N:30]([CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:29]1=[O:48])[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1C(=O)C2=CC=CC=C2C1=O)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(Cl)Cl.C(O)C>[NH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([NH:27][C@H:28]1[CH2:34][S:33][C@H:32]([C:35]2[S:36][CH:37]=[CH:38][CH:39]=2)[CH2:31][N:30]([CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:29]1=[O:48])[C:9]([O:8][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:10]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14234577HCID 14234577, compound

Product 1

HCID 14301775HCID 14301775, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

0.6 ml of hydrazine monohydrate was added to a solution of 815 mg of t-butyl α-{6(R)-[1(S)-t-butoxycarbonyl-5-phthalimidopentylamino]-5-oxo-2(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetate (prepared as described in Example 1) dissolved in a mixture of 3 ml of methylene chloride and 3 ml of ethanol, whilst ice-cooling, and the mixture was stirred at room temperature for 4 days. At the end of this time, the precipitate which appeared in the reaction mixture was filtered off and the filtrate was concentrated by evaporation under reduced pressure. The residue was mixed with ethyl acetate and the precipitated material was filtered off. The ethyl acetate filtrate was dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure to remove the solvent. The residue was subjected to column chromatography through silica gel using mixtures of ethyl acetate and methanol in the proportions 10:1 and 4:1 by volume as the eluent to yield 302 mg of the title compound as syrup.

Workup

  1. temperaturecooling
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. additionThe residue was mixed with ethyl acetate
  5. filtrationthe precipitated material was filtered off
  6. dry with materialThe ethyl acetate filtrate was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customto remove the solvent

Sources & evidence

ORD record
ord-b06a9c54d3824138b069de4b9faa646c
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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