HCID 69315473, compound → HCID 69317999, compound

HRID 271535Notes

Reaction equation

HRID 271535 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[O:18][C:19]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)=[C:20]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[C:27](=[O:31])[CH2:26][CH2:25]4)[CH:21]=2)[CH2:12]1)=O)C1C=CC=CC=1>C(O)C.C1CCCCC=1.[Pd]>[NH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[O:18][C:19]([C:32]3[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=3)=[C:20]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[C:27](=[O:31])[CH2:26][CH2:25]4)[CH:21]=2)[CH2:12]1

Participants

5

Reactant 1

HCID 69315473HCID 69315473, compound

Product 1

HCID 69317999HCID 69317999, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of the product of Step 5 (2.3 g, 4.67 mmol) in ethanol (100 ml) and cyclohexene (60 ml) was treated with 10% palladium on charcoal (0.8 g) and heated at 90° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was filtered through celite and washed several times with ethanol. The filtrate was evaporated in vacuo and the residue purified by silica gel chromatography eluting with chloroform/ethanol/0.880 ammonia solution (95:4.5:0.5) followed by (90:9:1) to yield the title compound (1.47 g, 88%); MS(ES+) m/e 359 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through celite
  3. washwashed several times with ethanol
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue purified by silica gel chromatography
  6. washeluting with chloroform/ethanol/0.880 ammonia solution (95:4.5:0.5)

Sources & evidence

ORD record
ord-a88f85a0f44c4770a0671cc5c39b0f13
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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