Tetrahydrofuran → HCID 70324238, compound

HRID 2081136Notes

Reaction equation

HRID 2081136 reaction equation
[C:1]([O:5]C([C@]1(C(O)=O)C[C@H]1CC)=O)([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:21]([N:23]2C=[N:26][CH:25]=[CH:24]2)=[O:22])C=1.[CH:28]1([S:31](N)(=[O:33])=[O:32])[CH2:30][CH2:29]1.[CH2:35]1CCN2[C:38](=NCCC2)[CH2:37][CH2:36]1.C1C[O:49]CC1>CCOC(C)=O>[CH:28]1([S:31]([NH:26][C:25]([C@@:24]2([NH:23][C:21](=[O:22])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:35][C@H:36]2[CH2:37][CH3:38])=[O:49])(=[O:33])=[O:32])[CH2:30][CH2:29]1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 67103077HCID 67103077, compound

Product 1

HCID 70324238HCID 70324238, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

(1R,2R)-1-(tert-butoxycarbonyl)-2-ethylcyclopropanecarboxylic acid (0.5 g, 2.18 mmol) was dissolved in THF (20 mL), followed by addition of CDI (390 mg, 2.41 mmol) in one portion at rt. The reaction was stirred in a 60° C. sandbath for 4 h, cooled to rt, and cyclopropanesulfonamide (292 mg, 2.41 mmol) and DBU (366 mg, 2.41 mmol) were added. The reaction was stirred at rt for overnight. The reaction was then diluted with EtOAc (30 mL) and washed with 1 N HCl (2×15 mL), water (10 mL), brine (10 mL), and dried (Na2SO4), giving tert-butyl (1R,2R)-1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropylcarbamate (0.53 g, 73% yield) as a white solid after removal of solvent. This crude product was directly used for the next without further purification.

Workup

  1. temperaturecooled to rt
  2. stirringThe reaction was stirred at rt for overnight
  3. washwashed with 1 N HCl (2×15 mL), water (10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-b5483f3d50344e079b05830a57500f96
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

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