4-Methylmorpholine → HCID 54195487, compound

HRID 1379394Notes

Reaction equation

HRID 1379394 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].Br[CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].CN1CCOCC1>O1CCOCC1>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH:6][CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62576Benzyl bromoacetateHCID 111190Methyl valinate hydrochloride

Product 1

HCID 54195487HCID 54195487, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.12 g (12.6 mmol) of L-valine methyl ester hydrochloride, 2.0 ml (12.6 mmol) of benzyl bromoacetate, and 3.5 ml (31 mmol) of 4-methylmorpholine in 100 ml of dioxane was heated at reflux for 4 h. After being allowed to cool, the solution was concentrated in vacuo and partitioned between ether and water. The organic layer was dried over MgSO4 and concentrated in vacuo. Chromatography on silica gel using 20% ethyl acetate in hexane provided 0.77 g (22%) of the desired compound as a colorless oil (Rf 0.24, 20% ethyl acetate in hexane). 1H NMR δ 0.95 (d, J=7 Hz, 6H), 1.96 (br, 1 H), 1.98 (octet, J=7 Hz, 1H), 3.08 (d, J=6 Hz, 1H), 3.43 (AA',2H), 3.71 (s, 3H), 5.16 (s, 2H), 7.36 (m, 5 H).

Workup

  1. temperatureat reflux for 4 h
  2. temperatureto cool
  3. concentrationthe solution was concentrated in vacuo
  4. custompartitioned between ether and water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb7c4c4ca3f14f7d9111feeb0755c4a0
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

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