1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69853422, compound

HRID 987935Notes

Reaction equation

HRID 987935 reaction equation
C(OP([CH2:9][C:10]([N:12]1[CH:16]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][O:14][C:13]1=[O:24])=[O:11])(=O)OCC)C.[Cl-].[Li+].N12CCCN=C1CCC[CH2:29][CH2:28]2.[C:38]([O:42][C:43]([N:45]1[C:49](CC=O)([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:48][O:47][C:46]1([CH3:61])[CH3:60])=[O:44])([CH3:41])([CH3:40])[CH3:39]>C(#N)C.C(OCC)C>[C:38]([O:42][C:43]([N:45]1[CH:49]([CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:48]([CH2:28][CH:29]=[CH:9][C:10]([N:12]2[CH:16]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:15][O:14][C:13]2=[O:24])=[O:11])[O:47][C:46]1([CH3:61])[CH3:60])=[O:44])([CH3:39])([CH3:40])[CH3:41]

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 20595745HCID 20595745, compoundHCID 86759215HCID 86759215, compound

Product 1

HCID 69853422HCID 69853422, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of [2-(4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-phosphonic acid diethyl ester (36.72 g) in dry acetonitrile (550 ml) was stirred at room temperature under nitrogen and treated with lithium chloride (4.39 g) followed by the dropwise addition of 1.8-diazabicyclo (5.4.0) undec-7-ene (g, mmol). After 5 minutes, the crude 4-benzyl-2,2-dimethyl-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester dissolved in dry acetonitrile (350 ml) was added via a cannula, and the resulting mixture was stirred at room temperature for 80 minutes. The mixture was then diluted with diethyl ether (1 L) and washed with brine (500 ml). The organic layer was dried (anhydrous magnesium sulfate) and concentrated in vacuo . Purification by flash chromatography on silica gel (ethyl acetate/hexane: 1/4 to 3/7) provided of 4-benzyl-5-[4-(4-benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-but-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (29.33 g, 69%).

Workup

  1. additionwas added via a cannula
  2. washwashed with brine (500 ml)
  3. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (ethyl acetate/hexane: 1/4 to 3/7)

Sources & evidence

ORD record
ord-c1dd61763fcf436a8d6ac9126c4755e5
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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