Morpholine → (4S)-1-t-Butoxycarbonyl-4-morpholino-N-t-butyl-L-prolinamide

HRID 1780275Notes

Reaction equation

HRID 1780275 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:19][C@H:18](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:17][C@H:9]1[C:10]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[C:1]([O:5][C:6]([N:8]1[CH2:19][C@@H:18]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH2:17][C@H:9]1[C:10]([NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86750836(4R)-1-t-butoxycarbonyl-4-(p-toluenesulfonyloxy)-N-t-butyl-L-prolinamide

Product 1

HCID 70048277(4S)-1-t-Butoxycarbonyl-4-morpholino-N-t-butyl-L-prolinamideYield 80.6%

Conditions

Temperature
80 °C

Procedure

A mixture of 1.0 g (2.27 mmol) of (4R)-1-t-butoxycarbonyl-4-(p-toluenesulfonyloxy)-N-t-butyl-L-prolinamide [prepared as described in step (a) above] and 5 g of morpholine was heated at 80° C. for 3 hours, whilst stirring. At the end of this time, the excess morpholine was removed by distillation under reduced pressure, and the residue was mixed with a saturated aqueous solution of sodium hydrogencarbonate. It was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized from a mixture of methylene chloride and diethyl ether, to give 650 mg of the title compound as colorless crystals, melting at 172°-173° C.

Workup

  1. customAt the end of this time, the excess morpholine was removed by distillation under reduced pressure
  2. additionthe residue was mixed with a saturated aqueous solution of sodium hydrogencarbonate
  3. extractionIt was then extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe resulting residue was recrystallized from a mixture of methylene chloride and diethyl ether

Sources & evidence

ORD record
ord-df59a3079fc84a3b8bb9a87f150f5512
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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