Triphenylphosphine → HCID 58822758, compound

HRID 459268Notes

Reaction equation

HRID 459268 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]([Si:19]([CH3:25])([CH3:24])[O:20][CH2:21][CH2:22][OH:23])([CH3:18])([CH3:17])[CH3:16].[CH2:26]([O:28][C:29](=[O:60])[C@@H:30]([O:58][CH3:59])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][O:42][C:43]2[CH:48]=[CH:47][C:46]([C:49](=[O:57])[C:50]3[CH:55]=[CH:54][C:53](O)=[CH:52][CH:51]=3)=[CH:45][CH:44]=2)=[CH:34][CH:33]=1)[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:26]([O:28][C:29](=[O:60])[C@@H:30]([O:58][CH3:59])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH2:40][CH2:41][O:42][C:43]2[CH:44]=[CH:45][C:46]([C:49](=[O:57])[C:50]3[CH:51]=[CH:52][C:53]([O:23][CH2:22][CH2:21][O:20][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:25])[CH3:24])=[CH:54][CH:55]=3)=[CH:47][CH:48]=2)=[CH:36][CH:37]=1)[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanolHCID 69426407HCID 69426407, compound

Product 1

HCID 58822758HCID 58822758, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diisopropyl azodicarboxilate (0.2 mmol, 0.04 mL) was added dropwise to a solution of 2-(tert-butyl-dimethyl-silanyloxy)-ethanol (0.26 mmol, 46 mg) (Example 122, Step A), (2S)-3-(4-{3-[4-(4-hydroxy-benzoyl)-phenoxy]-propoxy}-phenyl)-2-methoxy-propionic acid ethyl ester (0.13 mmol, 65 mg) and triphenylphosphine (0.2 mmol, 38 mg) in anhydrous toluene (2 mL) at 0° C. under nitrogen. The mixture was stirred overnight at room temperature, quenched with water and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under vacuum. The crude mixture was chromatographed on silica gel using a 4/1 hexane/EtOAc mixture as eluent to afford the title product 1H-NMR (200.15 MHz, CDCl3): δ 7.76 (d, 4H, J=8.9), 7.13 (d, 2H, J=8.6), 6.96 (d, 4H, J=8.6), 6.83 (d, 2H, J=8.6), 4.26–4.09 (m, 8H), 4.02–3.87 (m, 3H), 3.35 (s, 3H), 2.97 (m, 2H), 2.28 (qn, 2H, J=5.9), 1.23 (t, 3H, J=7.1), 0.91 (s, 9H), 0.11 (s, 6H).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude mixture was chromatographed on silica gel using a 4/1 hexane/EtOAc mixture as eluent

Sources & evidence

ORD record
ord-f51814cb7d5e4bd89983734e2b2f5ff5
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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