1,4-Dioxane → HCID 68862226, compound

HRID 2109410Notes

Reaction equation

HRID 2109410 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][C:12]([C:13]([NH:15][NH:16][C:17]([C:19]2[O:20][CH:21]=[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:18])=[O:14])=[CH:11][C:10]=1[O:38][CH3:39])C1C=CC=CC=1.O1CCOCC1>[C].[Pd].CO>[OH:8][C:9]1[CH:37]=[CH:36][C:12]([C:13]([NH:15][NH:16][C:17]([C:19]2[O:20][CH:21]=[C:22]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:18])=[O:14])=[CH:11][C:10]=1[O:38][CH3:39]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 68861926HCID 68861926, compound

Product 1

HCID 68862226HCID 68862226, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of the compound of Example 68 (0.80 g), dioxane (100 ml), methanol (10 ml) and 10% palladium carbon (0.16 g) was hydrogenated at 40° C. with stirred for 6 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methanol/chloroform=1/9) and recrystallized from ethanol, thereby giving 0.40 g of the desired compound. Melting point: 216-220° C.

Workup

  1. customwas hydrogenated at 40° C.
  2. filtrationThe reaction solution was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: methanol/chloroform=1/9)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-20bdf1ed737d48d986fd83aaf971407f
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

Loading…