Triphenylphosphine → HCID 69384193, compound

HRID 916830Notes

Reaction equation

HRID 916830 reaction equation
[CH3:1][C:2]1([CH3:27])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.O[CH2:29][CH2:30][O:31][CH2:32][C:33]1[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=1)[C:36]([O:38][CH3:39])=[O:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:27])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([O:26][CH2:29][CH2:30][O:31][CH2:32][C:33]5[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=5)[C:36]([O:38][CH3:39])=[O:37])=[CH:24][CH:25]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23344098HCID 23344098, compoundHCID 69384373HCID 69384373, compound

Product 1

HCID 69384193HCID 69384193, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(5R)-5(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-hydroxyphenyl)ethyl]-1,3-oxazolidin-2-one{Example 28 v)} (300 mg), methyl 3-[(2-hydroxyethoxy)methyl]benzoate (340 mg) and triphenylphosphine (642 mg) were dissolved in DCM (10 ml) and stirred for 15 min. To this was added 1,1′-(azodicarbonyl)dipiperidine (612 mg) and the solution was stirred for 16 h. The solution was then diluted in DCM, washed with water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (Biotage, 90 g) eluting with CH2Cl2-MeOH (250:1) to give the title compound (450 mg). LCMS RT=3.62 min.

Workup

  1. stirringthe solution was stirred for 16 h
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (Biotage, 90 g)
  6. washeluting with CH2Cl2-MeOH (250:1)

Sources & evidence

ORD record
ord-8f071fd45c3442bd868834ff2eea922a
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

Loading…