Calcium Carbonate → HCID 67304651, compound

HRID 61491Notes

Reaction equation

HRID 61491 reaction equation
I[C@@H:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@:3]12[CH2:11][C@H:7]([C:8](=[O:10])[O:9]1)[C@@H:6]([C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=3)[CH2:16][CH2:15]1)=[O:13])[CH2:5][CH2:4]2.C(=O)([O-])[O-].[Ca+2]>CCOC(C)=O.[Pd]>[CH2:2]([C@:3]12[CH2:11][C@H:7]([C:8](=[O:10])[O:9]1)[C@@H:6]([C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:16][CH2:15]1)=[O:13])[CH2:5][CH2:4]2)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 67304204(1s,2s,5s)-5-[(s)-Iodo(phenyl)methyl]-2-[4-(4-iodophenyl)piperazin-1-yl]carbonyl-6-oxabicyclo[3.2.1]octan-7-one

Product 1

HCID 67304651HCID 67304651, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (1S,2S,5S)-5-[(S)-iodo(phenyl)methyl]-2-[4-(4-iodophenyl)piperazin-1-yl]carbonyl-6-oxabicyclo[3.2.1]octan-7-one (49.0 mg, 0.0000747 mol) in ethyl acetate (5.0 mL, 0.051 mol) in a Parr bottle was added Calcium carbonate (15 mg, 0.00015 mol) and palladium (20 mg, 0.00002 mol) (as 10% Pd/C). The reaction mixture was stirred under hydrogen at 55 psi for 18 h. The reaction mixture was diluted with EtOAc, filtered through a pad of Celite and washed with EtOAc. The filtrate was concentrated in vacuo to give the crude product. (30 mg, 100% in yield). MS (ESI): (M+H)+=405.1.

Workup

  1. filtrationfiltered through a pad of Celite
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-84c821dd17b14803a8d591a9a785515d
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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