Ethyl Acetate → HCID 178467550, compound

HRID 2260487Notes

Reaction equation

HRID 2260487 reaction equation
C([O:8][CH2:9][N:10]1[C:25](=[O:26])[C:24]2[C:23]3[C:22]4[C:17](=[C:18]([O:27]CC5C=CC=CC=5)[CH:19]=[CH:20][CH:21]=4)[NH:16][C:15]=3[C:14]3[N:35]([C@:50]4([C:70](=[O:72])[CH3:71])[O:58][C@H:57]([CH2:59][OH:60])[C@@:55]([C:61](=[O:63])[CH3:62])([OH:56])[C@:53]([C:64](=[O:66])[CH3:65])([OH:54])[C@@:51]4([C:67](=[O:69])[CH3:68])[OH:52])[C:36]4[C:37]([O:42]CC5C=CC=CC=5)=[CH:38][CH:39]=[CH:40][C:41]=4[C:13]=3[C:12]=2[C:11]1=[O:73])C1C=CC=CC=1.C(OCC)(=O)C>[C].[Pd].C(O)C>[OH:42][C:37]1[C:36]2[N:35]([C@:50]3([C:70](=[O:72])[CH3:71])[O:58][C@H:57]([CH2:59][OH:60])[C@@:55]([C:61](=[O:63])[CH3:62])([OH:56])[C@:53]([C:64](=[O:66])[CH3:65])([OH:54])[C@@:51]3([C:67](=[O:69])[CH3:68])[OH:52])[C:14]3[C:15]4[NH:16][C:17]5[C:22](=[CH:21][CH:20]=[CH:19][C:18]=5[OH:27])[C:23]=4[C:24]4[C:25](=[O:26])[N:10]([CH2:9][OH:8])[C:11](=[O:73])[C:12]=4[C:13]=3[C:41]=2[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 131719227HCID 131719227, compound

Product 1

HCID 178467550HCID 178467550, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To 4.5 mg of 6-benzyloxymethyl-1,11-dibenzyloxy-12,13-dihydro-13-(tetraacetyl-β-D-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione were added 1.5 ml of ethyl acetate and 9 ml of ethanol to make a solution, and the solution was subjected to hydrogenation reaction in the presence of palladium-carbon catalyst (two medical spoonsful) for 3 hours. After the reaction, the palladium-carbon was removed by filtration and washed with methanol and tetrahydrofuran. The filtrate and the washings were concentrated under reduced pressure, the residue was subjected to thin layer chromatography (Kiesel gel 60; developed with chloroform-methanol=19:1), and the desired product was scraped and extracted with methanol to give 12,13-dihydro-1,11-dihydroxy-6-hydroxymethyl-13-(tetraacetyl-β-D-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (yield: 57.7%).

Workup

  1. customAfter the reaction
  2. customthe palladium-carbon was removed by filtration
  3. washwashed with methanol and tetrahydrofuran
  4. concentrationThe filtrate and the washings were concentrated under reduced pressure
  5. extractionextracted with methanol

Sources & evidence

ORD record
ord-30a7a88210bc4a6cad5f6475447898d6
Source dataset
uspto-grants-1995_12
Patent number
US05478813

Reaction notes

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