Thionyl Chloride → HCID 11322807, compound

HRID 2037285Notes

Reaction equation

HRID 2037285 reaction equation
C(OC([NH:8][C@@:9]1([C:23]([O:25][C:26](C)(C)[CH3:27])=[O:24])[CH2:14][C:13](=[O:15])[C@@H:12]2[C@H:10]1[C@H:11]2[C:16]([O:18][C:19](C)(C)[CH3:20])=[O:17])=O)(C)(C)C.S(Cl)(Cl)=O>C(O)C>[NH2:8][C@@:9]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:14][C:13](=[O:15])[C@@H:12]2[C@H:10]1[C@H:11]2[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59712878Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-, 2,6-bis(1,1-dimethylethyl) ester, (1S,2S,5R,6R)-

Product 1

HCID 11322807HCID 11322807, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Charge a 500 mL three neck flask equipped with a condenser, nitrogen inlet and a thermometer with ditert-butyl (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (15 g, 36.4 mmol) in ethanol (365 mL). Add thionyl chloride (13.3 mL, 182.3 mmol) to a stirring solution at room temperature via syringe (small exotherm) then heat to reflux. After 24 hours cool the reaction to room temperature and concentrate in vacuo. Dissolve the residue in dichloromethane (50 mL) then concentrate on a rotary evaporator (repeat 3 times). Partition the residue between ethyl acetate (200 mL) and saturated sodium hydrogenate carbonate (150 mL). Wash the organic phase with brine (150 mL), dry over sodium sulfate, filter then concentrate to dryness to give the title compound as an oil (8.24 g, 32.3 mmol). MS (m/z): 256 (M+1).

Workup

  1. customequipped with a condenser, nitrogen inlet
  2. temperatureAfter 24 hours cool
  3. customthe reaction to room temperature
  4. concentrationconcentrate in vacuo
  5. dissolutionDissolve the residue in dichloromethane (50 mL)
  6. concentrationthen concentrate on a rotary evaporator (repeat 3 times)
  7. customPartition the residue between ethyl acetate (200 mL) and saturated sodium hydrogenate carbonate (150 mL)
  8. washWash the organic phase with brine (150 mL)
  9. dry with materialdry over sodium sulfate
  10. filtrationfilter
  11. concentrationthen concentrate to dryness

Sources & evidence

ORD record
ord-6c697834ce3a4fa085c6c964a3d073d0
Source dataset
uspto-grants-2013_11
Patent number
US08575214B2

Reaction notes

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