HCID 131726351, compound → HCID 131726350, compound

HRID 1272577Notes

Reaction equation

HRID 1272577 reaction equation
C([O:8][C:9](=[O:38])[CH:10]([CH2:21][CH2:22][C:23]([CH:25]([OH:37])[C@H:26]1[O:32][C@:30]([CH3:33])([OH:31])[C@H:29]([OH:34])[C@@H:28]([OH:35])[C@@H:27]1[OH:36])=[O:24])[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1>CCO.CC(O)=O.[Pd]>[CH3:33][C@@:30]1([O:32][C@H:26]([CH:25]([C:23]([CH2:22][CH2:21][CH:10]([C:9]([OH:38])=[O:8])[C:11]([OH:13])=[O:12])=[O:24])[OH:37])[C@@H:27]([OH:36])[C@H:28]([OH:35])[C@H:29]1[OH:34])[OH:31]

Participants

5

Reactant 1

HCID 131726351HCID 131726351, compound

Product 1

HCID 131726350HCID 131726350, compoundYield 17.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of compound (69) (250 mg) in EtOH (20 mL) and AcOH (5 mL) was stirred under a hydrogen atmosphere (balloon) in the presence of 10% Pd/C (25 mg) for 4 h. After removal of the catalyst by filtration through celite, the filtrate was purified by preparative HPLC to provide the title compound (70) (29 mg) as a white solid. 1H NMR (CD3OD, 400 MHz): 4.65 (d, 1H), 4.40 (dd, 1H), 4.21 (dd, 1H), 3.65–3.76 (m, 1H), 3.58 (t, 1H), 3.36–3.50 (m, 1H), 3.39 (s, 3H), 3.25–3.35 (m, 1H), 2.46 (t, 2H), 2.14 (q, 2H).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration through celite
  3. customthe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-a1b9d17f9c694e6b97cf52b8492f4136
Source dataset
uspto-grants-2007_04
Patent number
US07208611B2

Reaction notes

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