Acetone → HCID 68736761, compound

HRID 451292Notes

Reaction equation

HRID 451292 reaction equation
C(C(CCCC)C([O-])=O)C.[Na+].[CH2:12]([O:19][N:20]1[C@H:25]2[CH2:26][N:22]([C@H:23]([C:27]([O:29]CC=C)=[O:28])[CH2:24]2)[C:21]1=[O:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)=O>O1CCCC1>[CH2:12]([O:19][N:20]1[C@H:25]2[CH2:26][N:22]([C@H:23]([C:27]([OH:29])=[O:28])[CH2:24]2)[C:21]1=[O:33])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 23672331Sodium 2-ethylhexanoateHCID 86659582HCID 86659582, compound

Product 1

HCID 68736761HCID 68736761, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium 2-ethylhexanoate (0.5 M in ethyl acetate, 2.5 mL, 1.25 mmol) was added to a solution of allyl (4R,6S)-3-(benzyloxy)-2-oxo-1,3-diazabicyclo[2.2.1]heptane-6-carboxylate (459 mg, 1.52 mmol), 1,1′-bis(diphenyl-phosphino)ferrocene-palladium(II)dichloride dichloromethane complex (116 mg, 0.14 mmol) in tetrahydrofuran (7.6 mL). The reaction mixture was stirred at room temperature for 2 hours (precipitate formed). Acetone (37 mL) was added. The resulting mixture was stirred at room temperature for 2 hours and the mixture was centrifuged. The solid was collected and washed with acetone and ether and dried under vacuum to afford the title compound as a tan solid. LC-MS (positive ionization) m/e 363 (M+H)

Workup

  1. custom(precipitate formed)
  2. stirringThe resulting mixture was stirred at room temperature for 2 hours
  3. customThe solid was collected
  4. washwashed with acetone and ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0001d83b901b4cdb9ceca16590cc324c
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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