4-Methylmorpholine → Tert-butyl 1-{3-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinylcarbonyl}piperidine-4carboxylate

HRID 977211Notes

Reaction equation

HRID 977211 reaction equation
CN1CCOCC1.[O:8]=[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][CH:23]([C:25]([OH:27])=O)[O:22][C:21]3=[O:28])=[CH:16][CH:15]=2)[NH:10]1.[NH:29]1[CH2:34][CH2:33][CH:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[O:8]=[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:24][CH:23]([C:25]([N:29]4[CH2:34][CH2:33][CH:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[O:27])[O:22][C:21]3=[O:28])=[CH:18][CH:19]=2)[NH:10]1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 1512676Tert-butyl Piperidine-4-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1360051203-[4-(5-Oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid

Product 1

HCID 136146332Tert-butyl 1-{3-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinylcarbonyl}piperidine-4carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.03 g of N-methylmorpholine are added to a solution of 2.91 g of 3-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid [obtainable according to Example 3], 2.77 g of tert-butyl piperidine-4-carboxylate, 2.02 g of 1-hydroxybenzotriazole and 2.86 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride in 20 ml of DMF, and the mixture is stirred at room temperature for 5 h. 200 ml of water are subsequently added dropwise with intensive stirring, the crystalline precipitate formed is separated off and taken up in 90 ml of dichloromethane, and the mixture is dried over Na2SO4. The solution is concentrated in vacuo, and the resulting oil is triturated with diethyl ether to give tert-butyl 1-{3-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinylcarbonyl}piperidine-4carboxylate, m.p. 171°-175°.

Workup

  1. customthe crystalline precipitate formed
  2. customis separated off
  3. dry with materialthe mixture is dried over Na2SO4
  4. concentrationThe solution is concentrated in vacuo
  5. customthe resulting oil is triturated with diethyl ether

Sources & evidence

ORD record
ord-e5b269ecef6f44c49d858bc5c9cc014d
Source dataset
uspto-grants-1997_03
Patent number
US05614535

Reaction notes

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