Triethylamine → Benzyl 2-{[(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]carbonyl}hydrazinecarboxylate

HRID 1168290Notes

Reaction equation

HRID 1168290 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C@H:9]1[C@@H:13]2[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]2[C@@H:11]([C:19]([OH:21])=O)[O:10]1.[C:22]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:25])[NH:23][NH2:24].C(N(CC)CC)C>ClCCl.O.C(OCC)(=O)C>[CH3:7][O:8][C@H:9]1[C@@H:13]2[O:14][C:15]([CH3:17])([CH3:18])[O:16][C@@H:12]2[C@@H:11]([C:19]([NH:24][NH:23][C:22]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[O:21])[O:10]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 79242Benzyl carbazateHCID 10932896ST092333

Product 1

HCID 59094496Benzyl 2-{[(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]carbonyl}hydrazinecarboxylateYield 96.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Oxalyl chloride (3.5 ml, 40 mmol) was added to a solution of (3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (Justus Liebigs Ann. Chem., 1974, 11, 1856) (3 g, 13.8 mmol) in dichloromethane (25 ml). The solution was stirred at room temperature for 3 hours and the solvent was then evaporated under reduced pressure. The acid chloride was re-dissolved in dichloromethane (25 ml) and treated with benzyl carbazate (2.3 g, 13.8 mmol) and triethylamine (5.7 ml, 41.4 mmol). After having been stirring at room temperature for 12 hours, the mixture was partioned between ethyl acetate (100 ml) and water (50 ml). The ethyl acetate layer was separated, washed with 1M aqueous citric acid solution (50 ml), saturated sodium hydrogencarbonate solution (50 ml) and brine (50 ml) and dried (anhydrous sodium sulphate). Evaporation of solvent under reduced pressure yielded the title compound as a yellow foam (4.87 g).

Workup

  1. customthe solvent was then evaporated under reduced pressure
  2. dissolutionThe acid chloride was re-dissolved in dichloromethane (25 ml)
  3. stirringAfter having been stirring at room temperature for 12 hours
  4. customThe ethyl acetate layer was separated
  5. washwashed with 1M aqueous citric acid solution (50 ml), saturated sodium hydrogencarbonate solution (50 ml) and brine (50 ml)
  6. dry with materialdried (anhydrous sodium sulphate)
  7. customEvaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-1777e081825e44b9b606ed6aaa1b3f34
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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