Propylene Oxide → HCID 66628397, compound

HRID 658535Notes

Reaction equation

HRID 658535 reaction equation
Cl.[CH2:2]([O:4][C:5]([C@:7]1([F:27])[C@@H:12]2[C@H:8]1[CH2:9][C@@H:10]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[C@@:11]2([NH2:16])[C:13]([OH:15])=[O:14])=[O:6])[CH3:3].C1OC1C>C(O)C>[CH2:2]([O:4][C:5]([C@:7]1([F:27])[C@@H:12]2[C@H:8]1[CH2:9][C@@H:10]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[C@@:11]2([NH2:16])[C:13]([OH:15])=[O:14])=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 66628396HCID 66628396, compound

Product 1

HCID 66628397HCID 66628397, compoundYield 62,660.801%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

400 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-ethyl ester hydrochloride was added to a mixture of 5 mL of ethanol and 5 mL of propyleneoxide, and the mixture was heated to redux for 2.5 hours. After standing to cool, the precipitated solids were filtered, and the solids were washed with diethyl ether and then recrystallized from water: ethanol, thereby yielding 230 g of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-ethyl ester.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool
  3. filtrationthe precipitated solids were filtered
  4. washthe solids were washed with diethyl ether
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-469417b97e41497fb4ce3fd6d6032b59
Source dataset
uspto-grants-2011_12
Patent number
US08076502B2

Reaction notes

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