4-Methylmorpholine → HCID 131721726, compound
Reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].O.C[N:19]1CCOCC1.ClC(OCC(C)C)=O.Cl.[CH3:34][NH:35][O:36][CH3:37]>C1COCC1>[CH3:34][N:35]([C:7](=[O:9])[C@H:2]([CH2:3][CH:4]([CH3:5])[CH3:6])[N:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[NH2:19])[O:36][CH3:37]Participants
Conditions
- Temperature
- -10 °C
Procedure
A solution of Boc-Leu-OH.H2O (80.3 mmol) and N-methyl morpholine (88 mmol) in THF (35 ml) was added to a pre cooled solution of isobutyl chloroformate (88 mmol) in THF (65 ml) under nitrogen at between -10 and -15° C. over 40 minutes. The reaction was stirred at -10° C. for 1 hour after which time N-methyl morpholine (88 mmol) was added followed by N,O-Dimethylhydroxylamine hydrochloride (88 mmol) portion wise between -10 and 0° C. The reaction was then stirred at -10° C. for 1 hour and then allowed to warm up to room temperature over night. The THF was then removed under vacuum and water (50 ml) and ethylacetate (200 ml) added. The organic layer was then washed with 0.1 M citric acid solution (4×50 ml), then saturated sodium bicarbonate (4×50 ml), dried over magnesium sulphate and then concentrated under vacuum to give the product.
Workup
- additionwas added
- temperatureto warm up to room temperature over night
- customThe THF was then removed under vacuum and water (50 ml) and ethylacetate (200 ml)
- additionadded
- washThe organic layer was then washed with 0.1 M citric acid solution (4×50 ml)
- dry with materialsaturated sodium bicarbonate (4×50 ml), dried over magnesium sulphate
- concentrationconcentrated under vacuum
- customto give the product
Sources & evidence
- ORD record
- ord-b25ab7dc275d4747942468ef093b9fe2
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06034066
Reaction notes
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