HCID 77768281, compound → HCID 77767970, compound

HRID 2230324Notes

Reaction equation

HRID 2230324 reaction equation
[C:1]([NH:5][C:6]([CH:8]([NH:24][C:25]([CH:27]([NH:32][C:33]([N:35]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:34])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CO.[Pd]>[C:1]([NH:5][C:6]([CH:8]([NH:24][C:25]([CH:27]([NH:32][C:33]([N:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1)=[O:34])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:15]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 77768281HCID 77768281, compound

Product 1

HCID 77767970HCID 77767970, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the product from Example 134 (0.187 g, 0.33 mmol) in 16 mL of 1:1 THF/methanol mixture was added 20% Pd/C (0.1 g). The resulting solution was hydrogenated for 20.5 hours at 20 psi. The crude mixture was evaporated to dryness and was purified by chromatography (silica gel, 30% ethyl acetate/hexane). It was further purified by crystallizing from petroleum ether and toluene to give the title compound (0.12 g, 65%) as a white solid, mp 155-156° C. Anal. Calc'd for C34H50N4O3: C, 72.56; H, 8.95; N, 9.95. Found: C, 72.2; H, 9.03; N, 9.80

Workup

  1. customThe crude mixture was evaporated to dryness
  2. customwas purified by chromatography (silica gel, 30% ethyl acetate/hexane)
  3. customIt was further purified
  4. customby crystallizing from petroleum ether and toluene

Sources & evidence

ORD record
ord-2e100f20118640d980a3f40a1c8df859
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

Loading…