Hydrazine hydrate (1:1) → (E)-2'-(2-aminoethanesulphonyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

HRID 1386563Notes

Reaction equation

HRID 1386563 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:48][CH:49]([CH3:51])[CH3:50])[C:22]([NH:24][N:25]([CH2:44][CH:45]([CH3:47])[CH3:46])[S:26]([C:29](=O)[CH2:30][N:31]1C(=O)C2C(=O)C=CC=C2C1=O)(=[O:28])=[O:27])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].O.NN>C(O)C>[NH2:31][CH2:30][CH2:29][S:26]([N:25]([CH2:44][CH:45]([CH3:47])[CH3:46])[NH:24][C:22](=[O:23])[C@@H:21]([C@@H:11]([C:9](=[O:10])[NH:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:48][CH:49]([CH3:51])[CH3:50])(=[O:28])=[O:27]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86757181HCID 86757181, compound

Product 1

HCID 86757180(E)-2'-(2-aminoethanesulphonyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazideYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.46 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-(1,3-dioxo-2-phthalimidoethansulphonyl)-4-methylvalerohydrazide in 10 ml of ethanol was treated with 4.5 ml of hydrazine hydrate and stirred at room temperature for 2 hours. Evaporation gave a residue which was triturated with ethyl acetate and filtered. The filtrate was washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulphate. The residue was purified by column chromatography on silica gel using methanol/dichloromethane (5:95) for the elution to give 0.26 g of (E)-2′-(2-aminoethanesulphonyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a pale yellow gum.

Workup

  1. customEvaporation
  2. customgave a residue which
  3. customwas triturated with ethyl acetate
  4. filtrationfiltered
  5. washThe filtrate was washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customThe residue was purified by column chromatography on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-45f7a6ca4f5f4dde806c4f819fbc0b88
Source dataset
uspto-grants-2001_07
Patent number
US06265446B1

Reaction notes

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