HCID 86641034, compound → HCID 24986794, compound

HRID 333656Notes

Reaction equation

HRID 333656 reaction equation
COC1C=CC(C[O:8][C@H:9]([C@H:63]([O:78]CC2C=CC(OC)=CC=2)[CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[C@@H:10]([N:52]2[CH:56]=[C:55]([CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[N:54]=[N:53]2)[CH2:11][O:12][C@@H:13]2[C@H:18]([O:19]CC3C=CC=CC=3)[C@@H:17]([O:27]CC3C=CC=CC=3)[C@@H:16]([O:35]CC3C=CC=CC=3)[CH:15]([CH2:43][O:44]CC3C=CC=CC=3)[O:14]2)=CC=1.[H][H]>C(O)C.C(Cl)Cl.[OH-].[OH-].[Pd+2]>[CH2:57]([C:55]1[N:54]=[N:53][N:52]([C@H:10]([C@H:9]([OH:8])[C@H:63]([OH:78])[CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[CH2:11][O:12][C@@H:13]2[C@H:18]([OH:19])[C@@H:17]([OH:27])[C@@H:16]([OH:35])[CH:15]([CH2:43][OH:44])[O:14]2)[CH:56]=1)[CH2:58][CH2:59][CH2:60][CH2:61][CH3:62]

Participants

5

Reactant 2

HCID 86641034HCID 86641034, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24986794HCID 24986794, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

The compound (1.0 eq.) obtained in Step 1 was dissolved in a mixed solvent of ethylalcohol/methylene chloride (3:1, 0.01˜0.1 M) to which Pd(OH)2 (500 massa) was then added. The resulting reaction mixture was stirred for 5˜8 hrs at room temperature under 1 atm of hydrogen gas. After the filtration of the metal catalyst through a Celite pad, the reaction mixture was washed with a solution of ethylalcohol/methylene:chloride (3:1). After two rounds of centrifugation at 1000 rpm for 10 min, the supernatant was concentrated and dried in a vacuum. The concentrate was precipitated in a mixed solvent of hexane/ethyl acetate (1:1) to afford the object compound as a white wax solid (24 mg, 80%).

Workup

  1. additionwas then added
  2. customThe resulting reaction mixture
  3. filtrationAfter the filtration of the metal catalyst through a Celite pad
  4. washthe reaction mixture was washed with a solution of ethylalcohol/methylene
  5. concentrationthe supernatant was concentrated
  6. customdried in a vacuum
  7. customThe concentrate was precipitated in a mixed solvent of hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-bd712470620f4f0ba317dc6b2524cd65
Source dataset
uspto-grants-2014_11
Patent number
US08883746B2

Reaction notes

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