Hydrochloric Acid → HCID 71695828, compound

HRID 2037292Notes

Reaction equation

HRID 2037292 reaction equation
C(OC([NH:8][C@@:9]1([C:24]([O:26]C(C)(C)C)=[O:25])[CH2:16][C:13]2([CH2:15][CH2:14]2)[C@@H:12]2[C@H:10]1[C@H:11]2[C:17]([O:19]C(C)(C)C)=[O:18])=O)(C)(C)C.[ClH:31]>O1CCOCC1>[ClH:31].[NH2:8][C@@:9]1([C:24]([OH:26])=[O:25])[CH2:16][C:13]2([CH2:15][CH2:14]2)[C@@H:12]2[C@H:10]1[C@H:11]2[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86691260HCID 86691260, compound

Product 1

HCID 71695828HCID 71695828, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Charge a 5 mL ReactiVial with ditert-butyl (1S,2S,5R,6S)-2-(tert-butoxycarbonylamino)spiro[bicyclo[3.1.0]hexane-4,1′-cyclopropane]-2,6-dicarboxylate (55 mg, 129.8 μmol). To this add a 5N aqueous hydrochloric acid solution (3 mL; 20.8 mmol) and 1,4-dioxane (1 mL). Stir the mixture at 90° C. for one hour. Seal the ReactiVial and continue stirring at 90° C. for 3 hours. Cool to ambient temperature and stand for 3 days. Concentrate under reduced pressure to a dark solid. Prepare a Oasis® HLB Waters (1 g) cartridge by washing with 2 column volumes of methanol, followed by 6 column volumes of water. Dissolve the dark solid in water and load onto the cartridge. Wash the cartridge with water (2 column volumes) and collect the eluent. Freeze-dry the solution to yield title compound (16.1 mg, 65 μmol). MS (m/z): 212 (M+1). 1H NMR (D2O) δ 0.45 (m, 1H), 0.53 (m, 1H), 0.64 (m, 1H), 0.74 (m, 1H), 1.72-1.78 (m, 2H) 1.86 (d, J=14.2 Hz, 1H), 2.07 (m, 1H), 2.37 (m, 1H).

Workup

  1. customSeal the ReactiVial
  2. stirringcontinue stirring at 90° C. for 3 hours
  3. temperatureCool to ambient temperature
  4. waitstand for 3 days
  5. concentrationConcentrate under reduced pressure to a dark solid
  6. customPrepare a Oasis® HLB Waters (1 g) cartridge
  7. washby washing with 2 column volumes of methanol
  8. dissolutionDissolve the dark solid in water
  9. washWash the cartridge with water (2 column volumes)
  10. customcollect the eluent
  11. customFreeze-dry the solution

Sources & evidence

ORD record
ord-4b8f88de4cdd49cd923b15034bdfb74c
Source dataset
uspto-grants-2013_11
Patent number
US08575214B2

Reaction notes

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