HCID 86600751, compound → HCID 11215979, compound

HRID 2252457Notes

Reaction equation

HRID 2252457 reaction equation
C([O:8][C@@H:9]1[C@@H:16]([O:17]CC2C=CC=CC=2)[C@H:15]([O:25]CC2C=CC=CC=2)[C@@H:14]([CH2:33][O:34][C:35]2[CH:36]=[C:37]([C:41]3[CH:46]=[CH:45][C:44]([C@@H:47]4[C@@H:50]([CH2:51][CH2:52][C@@H:53]([C:55]5[CH:60]=[CH:59][C:58]([F:61])=[CH:57][CH:56]=5)[OH:54])[C:49](=[O:62])[N:48]4[C:63]4[CH:68]=[CH:67][C:66]([F:69])=[CH:65][CH:64]=4)=[CH:43][CH:42]=3)[CH:38]=[CH:39][CH:40]=2)[O:13][C@@H:10]1[O:11][CH3:12])C1C=CC=CC=1>C(O)C.[Pd]>[F:69][C:66]1[CH:67]=[CH:68][C:63]([N:48]2[C:49](=[O:62])[C@H:50]([CH2:51][CH2:52][C@@H:53]([C:55]3[CH:56]=[CH:57][C:58]([F:61])=[CH:59][CH:60]=3)[OH:54])[C@H:47]2[C:44]2[CH:43]=[CH:42][C:41]([C:37]3[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH2:33][C@H:14]4[O:13][C@H:10]([O:11][CH3:12])[C@H:9]([OH:8])[C@@H:16]([OH:17])[C@@H:15]4[OH:25])[CH:36]=3)=[CH:46][CH:45]=2)=[CH:64][CH:65]=1

Participants

4

Reactant 1

HCID 86600751HCID 86600751, compound

Product 1

HCID 11215979HCID 11215979, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 2,3,4-tri-O-benzyl-6-O-(4′-{(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}biphenyl-3-yl)-α-D-glucopyranoside (70 mg, 0.08 mmol) was dissolved in absolute ethanol (3 mL). 10% Pd/C (wet, 14% w/w) was added and the vessel sealed. The solution was degassed by evacuation and flushing with hydrogen gas at balloon pressure. The reaction was monitored by TLC (1:1 hexane-ethyl acetate). Upon completion, the catalyst was filtered by passing through a plug of Celite® and washing with additional ethanol. The filtrate was concentrated in vacuo and purified by preparative HPLC (Polaris C18-A 10 μ 250×21.2 mm column, 30% to 95% acetonitrile-0.1% trifluoroacetic acid in water) affording methyl 6-O-(4′-{(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}biphenyl-3-yl)-α-D-glucopyranoside (18.1 mg, 36% yield); 1H NMR (300 MHz, CDCl3/1% CD3OD) δ 7.58 (d, J=8.4 Hz, 2H), 7.38-7.23 (m, 7H), 7.17-7.14 (m, 2H), 7.04-6.92 (m, 5H), 4.80 (d, J=3.9 Hz, 1H), 4.70 (d, J=2.4 Hz, 1H), 4.67 (t, J=5.7 Hz, 1H), 4.37-4.33 (m, 1H), 4.26-4.21 (m, 1H), 3.92-3.87 (m, 1H), 3.74-3.45 (m, 3H), 3.42 (s, 3H), 3.18-3.10 (m, 1H), 2.01-1.88 (m, 4H) ppm; MS [M−OH]+ 644.0.

Workup

  1. customthe vessel sealed
  2. customThe solution was degassed by evacuation
  3. customflushing with hydrogen gas at balloon pressure
  4. filtrationUpon completion, the catalyst was filtered
  5. washwashing with additional ethanol
  6. concentrationThe filtrate was concentrated in vacuo
  7. custompurified by preparative HPLC (Polaris C18-A 10 μ 250×21.2 mm column, 30% to 95% acetonitrile-0.1% trifluoroacetic acid in water)

Sources & evidence

ORD record
ord-ff1b152de3d6417691fccfeb844639d0
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

Loading…