Hydrazine hydrate (1:1) → HCID 70155369, compound

HRID 1599490Notes

Reaction equation

HRID 1599490 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C@H:31]2[CH2:35][CH2:34][C@H:33]([C:36]3[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44][CH3:45])=[C:38]([O:46][CH3:47])[CH:37]=3)[O:32]2)[CH:8]=[C:9]([O:15][CH2:16][C:17]#[C:18][CH2:19][N:20]2C(=O)C3=CC=CC=C3C2=O)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])(=[O:4])=[O:3].O.NN>C(O)C>[NH2:20][CH2:19][C:18]#[C:17][CH2:16][O:15][C:9]1[CH:8]=[C:7]([C@H:31]2[CH2:35][CH2:34][C@H:33]([C:36]3[CH:37]=[C:38]([O:46][CH3:47])[C:39]([O:44][CH3:45])=[C:40]([O:42][CH3:43])[CH:41]=3)[O:32]2)[CH:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:10]=1[O:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58753263HCID 58753263, compound

Product 1

HCID 70155369HCID 70155369, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trans-2-[3-methylsulfonyl-5-(4-phthalimido-but-2-ynyloxy)-4-propyloxyphenyl]-5-(3,4,5-trimethoxyphenyl)-tetrahydrofuran. (244, whole amount obtained from the previous step) in ethanol (5.0 mL) was added hydrazine hydrate (136 mL, 2.8 mmol). The resulting solution was refluxed overnight. The ethanol was removed in vacuo and the residue was diluted with methylene chloride (25 mL) and water (25 mL). The layers were separated and the water layer was extracted with methylene chloride (25 mL). The combined organic extracts were dried and concentrated in vacuo. The residue was purified using PLC (eluent, 5% methanol in methylene chloride) to obtain 75 mg (50% overall from 242) of trans-2-[3-(4-amino-but-2-ynyloxy) -5-methylsulfonyl-4-propyloxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (244). 1H-NMR (CDCl3) δ7.55 (1H, d, J=2.0 Hz), 7.37 (1H, d, J=2.0 Hz), 6.59 (2H, s), 5.16-5.28 (2H, m), 4.79 (2H, s), 4.12 (2H, t, J=6.6 Hz), 3.87 (6H, s), 3.81 (3H, s), 3.44 (2H, s), 3.23 (3H, s), 2.43-2.50 (2H, m), 1.83-2.03 (4H, m), 1.57 (2H, brs), 1.04 (3H, t, J=6.6 Hz).

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. customThe ethanol was removed in vacuo
  3. additionthe residue was diluted with methylene chloride (25 mL) and water (25 mL)
  4. customThe layers were separated
  5. extractionthe water layer was extracted with methylene chloride (25 mL)
  6. customThe combined organic extracts were dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified

Sources & evidence

ORD record
ord-91a6bb7e6d6d4077a4c5453eda3cb7f8
Source dataset
uspto-grants-1998_04
Patent number
US05741809

Reaction notes

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