1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 9802536, compound

HRID 1584312Notes

Reaction equation

HRID 1584312 reaction equation
[C:1]([O:4][C@H:5]([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)[O:24][C:25]=2[CH3:26])=[C:15]([O:32][CH3:33])[CH:14]=1)[C:6](OC)=[O:7])(=[O:3])[NH2:2].C1CCN2C(=NCCC2)CC1>C(Cl)(Cl)Cl>[O:28]1[CH:29]=[CH:30][CH:31]=[C:27]1[C:23]1[O:24][C:25]([CH3:26])=[C:21]([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][C@H:5]3[O:4][C:1](=[O:3])[NH:2][C:6]3=[O:7])=[CH:14][C:15]=2[O:32][CH3:33])[N:22]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11123358HCID 11123358, compound

Product 1

HCID 9802536HCID 9802536, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl (R)-(+)-2-carbamoyloxy-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]pentanoate (2.92 g) in chloroform (100 ml) was added dropwise, at temperature ranging from -5 to 0° C., 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) (1.54 g). The mixture was stirred for one hour at the same temperature range. The reaction mixture was washed with 2N HCl and water, which was then dried (MgSO4) and concentrated to yield (R)-(+)-5-[3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]propyl]-2,4-oxazolidinedione (2.46 g, 91%), which was recrystallized from acetone-isopropyl ether to give colorless needles, m.p.122-123° C. [α]D +39.4° (c=0. 495, CHCl3)

Workup

  1. customranging from -5 to 0° C.
  2. washThe reaction mixture was washed with 2N HCl and water, which
  3. dry with materialwas then dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c71c1b70f1464b31bfec3061f90ef213
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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