Hydrazine hydrate (1:1) → HCID 18657915, compound

HRID 1755755Notes

Reaction equation

HRID 1755755 reaction equation
O.[NH2:2][NH2:3].C([O:6][C:7](=O)[CH:8]=[CH:9][C@@H:10]1[CH2:14][C@H:13]([S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][N:11]1[C:35]([O:37][CH2:38][CH:39]=[CH2:40])=[O:36])C>C(O)C>[CH2:38]([O:37][C:35]([N:11]1[CH2:12][C@@H:13]([S:15][C:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:14][C@H:10]1[CH:9]1[NH:3][NH:2][C:7](=[O:6])[CH2:8]1)=[O:36])[CH:39]=[CH2:40]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67750135HCID 67750135, compound

Product 1

HCID 18657915HCID 18657915, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (0.61 ml, 12.6 mmol) was dropwise added to a solution of 3-[(2S,4S)-N-allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]acrylic acid ethyl ester (1.53 g, 2.9 mmol) in ethanol (7.5 ml) under cooling with ice, and the mixture was stirred at the same temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, 2% methanol-chloroform) to obtain (2S,4S)-N-allyloxycarbonyl-2-(3-pyrazolidinon-5-yl)-4-tritylthiopyrrolidine (830 mg, yield: 51.1%). This compound was immediately dissolved in methylene chloride (10 ml). Then, triethylamine (0.24 ml, 1.7 mmol) and allyl chloroformate (0.18 ml, 1.7 mmol) were dropwise added thereto under cooling with ice, and the mixture was stirred at the same temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and the residue was extracted with ethyl acetate (50 ml). The organic layer was washed with water and a saturated sodium chloride aqueous solution, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, 1% methanol-chloroform) to obtain (2S,4S)-N-allyloxycarbonyl-2-(1-allyloxycarbonyl-3-pyrazolidinon-5-yl)-4-tritylthiopyrrolidine (592 mg, yield: 62%).

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-342bd47c72854051aa2e260b1e601602
Source dataset
uspto-grants-1995_08
Patent number
US05438054

Reaction notes

Loading…