Morpholine → N-[N-benzyloxycarbonyl-L-prolyl]morpholine

HRID 429753Notes

Reaction equation

HRID 429753 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 13564348N-[N-benzyloxycarbonyl-L-prolyl]morpholineYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-benzyloxycarbonyl-L-proline (5 g, 20.06 mmol), morpholine (1.92 ml, 20.06 mmol), and N-hydroxysuccinimide (2.31 g, 20.06 mmol) in N, N-dimethylformamide (100 ml) was added DCC (4.14 g, 20.06 mmol) and the resulting mixture was stirred for 4 h at room temperature. After the precipitation was filtered off, the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate and the resulting precipitation was filtered off. After the filtrate was washed with dilute hydrochloric acid, saturated sodium hydrogencarbonate aq., and water, the organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized from the mixed solvents of ethyl acetate-hexane to give the compound (34) (4.44 g, 69.5%).

Workup

  1. customAfter the precipitation
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. customthe resulting precipitation
  6. filtrationwas filtered off
  7. washAfter the filtrate was washed with dilute hydrochloric acid, saturated sodium hydrogencarbonate aq., and water
  8. dry with materialthe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized from the mixed solvents of ethyl acetate-hexane

Sources & evidence

ORD record
ord-918a80e19f184c84a99dbd9be477e862
Source dataset
uspto-grants-2001_11
Patent number
US06319902B1

Reaction notes

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