Ethanol → HCID 69220851, compound

HRID 1269018Notes

Reaction equation

HRID 1269018 reaction equation
CC(C)C(N[C:16]([CH:18]1[CH2:22][CH:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][N:19]1[CH2:28][C:29]1[N:30]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:31]=[CH:32][N:33]=1)=[O:17])C1C(O)C(O)C(O)C(SC)O1.C1CC=CCC=1.CC[OH:50]>[Pd]>[CH2:34]([N:30]1[CH:31]=[CH:32][N:33]=[C:29]1[CH2:28][N:19]1[CH2:20][CH:21]([CH2:23][CH:24]=[CH:25][CH2:26][CH3:27])[CH2:22][CH:18]1[C:16]([OH:50])=[O:17])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 123431,4-CyclohexadieneHCID 86596638HCID 86596638, compound

Product 1

HCID 69220851HCID 69220851, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To an oven dried sealed tube, was added a solution of the above crude 1-(1-Benzyl-1H-imidazol-2-ylmethyl)-4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide (280 mg, 0.48 mmol) in anhydrous EtOH (5 mL), 10% Pd on carbon (560 mg) and 1,4-cyclohexadiene (1.5 mL). The reaction vessel was purged with N2, sealed and stirred at room temperature for 18 h. The reaction mixture was filtered through celite, washed several times with reagent alcohol, and the combined washings and filtrate were evaporated to dryness. The resulting residue was purified by silica gel chromotography (1:9 methanolic ammonia/CH2Cl2). The desired fractions were evaporated to dryness and lyophilized, to furnish the title compound for example 42 (29.3 mg, 18%): TLC Rf=0.7 (14% methanolic ammonia/CH2Cl2), KMnO4 visualization stain; MS (ESPOS): 499.4 [M+H]+

Workup

  1. customTo an oven dried
  2. customsealed tube
  3. customThe reaction vessel was purged with N2
  4. customsealed
  5. filtrationThe reaction mixture was filtered through celite
  6. washwashed several times with reagent alcohol
  7. customthe combined washings and filtrate were evaporated to dryness
  8. customThe resulting residue was purified by silica gel chromotography (1:9 methanolic ammonia/CH2Cl2)
  9. customThe desired fractions were evaporated to dryness

Sources & evidence

ORD record
ord-aec6851fba49409586546318cf4a0dde
Source dataset
uspto-grants-2007_04
Patent number
US07199106B2

Reaction notes

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