Triethylamine → HCID 22876691, compound

HRID 1377927Notes

Reaction equation

HRID 1377927 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:21]=[CH:20][C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.C([Li])CCC.[CH2:41]([C@H:48]1[CH2:52][O:51][C:50](=[O:53])[NH:49]1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.O1CCNC1=O>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]([N:49]3[C@@H:48]([CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH2:52][O:51][C:50]3=[O:53])=[O:19])=[CH:20][CH:21]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 739492-OxazolidinoneHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 22915493HCID 22915493, compoundHCID 178418339Butyllithium

Product 1

HCID 22876691HCID 22876691, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a -70° C. solution in THF (100 mL) of 4-[4-(4-cyanophenyl)phenoxy]butanoic acid (1.00 g, 3.66 mmol), prepared as in Example 3, was added triethylamine (0.64 mL, 4.62 mmol) and pivaloyl chloride (0.49 mL, 3.91 mmol). The reaction mixture was stirred for 15 minutes at -70° C., 45 minutes at 0° C., and then was cooled back to -70° C. In a separate flask, n-butyllithium (2.5M in hexanes, 2.56 mL, 6.40 mmol) was added via syringe to a -78° C. a solution in THF (50 mL) of (S)-(-)-4-benzyl-2-oxazolidinone. The oxazolidinone anion solution was then added to the mixed anhydride solution via cannula. The reaction mixture was then warmed slowly to ambient temperature and stirred overnight. The reaction mixture was quenched with aqueous 1M HCl and extracted with ethyl ether. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting white solid was azeotroped with ethyl ether and purified by chromatography on silica gel (2% methanol-dichloromethane) to give N-[4-(4-(4-cyanophenyl)phenoxy)butanoyl]-(S)-(-)-4-benzyl-2-oxazolidinone (1.30 g, 82%).

Workup

  1. temperaturewas cooled back to -70° C
  2. temperatureThe reaction mixture was then warmed slowly to ambient temperature
  3. stirringstirred overnight
  4. customThe reaction mixture was quenched with aqueous 1M HCl
  5. extractionextracted with ethyl ether
  6. washThe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting white solid was azeotroped with ethyl ether
  11. custompurified by chromatography on silica gel (2% methanol-dichloromethane)

Sources & evidence

ORD record
ord-b6b93fb26fcd48d5b52ed3f1993e72bb
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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