HCID 86654421, compound → HCID 86654422, compound

HRID 2067854Notes

Reaction equation

HRID 2067854 reaction equation
[C:1]([O:4][C:5]1([C@@:9]2([C:29]([O:31]CC3C=CC=CC=3)=[O:30])[CH2:13][C@H:12]([N:14]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[C@@H:15]3[C@H:20]([O:21][CH3:22])[CH2:19][O:18][CH2:17][CH2:16]3)[CH:11]=[CH:10]2)[CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].[H][H]>C(O)(=O)C.[Pt].[Pd]>[C:1]([O:4][C:5]1([C@:9]2([C:29]([OH:31])=[O:30])[CH2:10][CH2:11][C@@H:12]([N:14]([C:23](=[O:28])[C:24]([F:27])([F:25])[F:26])[C@@H:15]3[C@H:20]([O:21][CH3:22])[CH2:19][O:18][CH2:17][CH2:16]3)[CH2:13]2)[CH2:6][CH2:7][CH2:8]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 86654421HCID 86654421, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86654422HCID 86654422, compoundYield 103%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2.62 g (4.86 mmol) of 3-[{(1S,4R)-4-[1-(acetyloxy)cyclobutyl]-4-[(benzyloxy)carbonyl]cyclopent-2-en-1-yl}(trifluoroacetyl)amino]-1,5-anhydro-2,3-dideoxy-4-O-methyl-D-erythro-pentitol and 750 mg each of 5% Pt/C and 5% Pd/C in 10 mL of acetic acid was stirred rapidly under 50 psi hydrogen gas for 18 h, then filtered through diatomaceous earth to remove catalyst. The filtrate was concentrated under reduced pressure, with added toluene to azeotropically remove acetic acid, to provide 2.25 g (103%) of the title compound as a white foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.50-1.71 (m, 3H) 1.74-1.84 (m, 1H) 2.02 (s, 3H) 2.04-2.17 (m, 1H) 2.34-2.55 (m, 5H) 2.60 (dd, J=14.3, 8.5 Hz, 1H) 2.66-2.81 (m, 2H) 3.30 (d, J=13.0 Hz, 1H) 3.35-3.39 (m, 1H) 3.42 (s, 3H) 3.47-3.56 (m, 1H) 3.83-3.91 (m, 1H) 4.13 (dd, J=11.6, 4.4 Hz, 1H) 4.16-4.23 (m, 1H) 4.26-4.38 (m, 1H). LC-MS ES+ 452.1.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. customto remove catalyst
  3. concentrationThe filtrate was concentrated under reduced pressure, with added toluene to azeotropically remove acetic acid

Sources & evidence

ORD record
ord-49c548867e5e4ddab6ad33cfc930031a
Source dataset
uspto-grants-2012_10
Patent number
US08293903B2

Reaction notes

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