4-Methylmorpholine → HCID 10404865, compound

HRID 1162842Notes

Reaction equation

HRID 1162842 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:19]([OH:21])=O)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:23][NH:24][O:25][CH3:26].CN1CCOCC1>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@@H:10]([C:19]([N:24]([O:25][CH3:26])[CH3:23])=[O:21])[NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 10404865HCID 10404865, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of O-benzyl-N-(tert-butoxycarbonyl)serine (5.9 g, 20.0 mmol) in CH2Cl2 (20 mL) was added N,O-dimethylhydroxylamine hydrochloride (1.95 g, 20.0 mmol) followed by N-methylmorpholine (2.20 mL, 19.98 mmol). The mixture was cooled to 0° C. and treated with a 1 M solution of N,N-dicyclohexylcarbodiimide in CH2Cl2 (20.0 mL, 20.0 mmol). The mixture was allowed to warm to ambient temperature while stirring under inert atmosphere for 18 h. The mixture was filtered, washing the solid residue with excess CH2Cl2, and the filtrate was concentrated in vacuo. The resulting oil was suspended in EtOAc, stirred for 20 min, and filtered once more, washing with EtOAc. The filtrate was concentrated to an orange oil which was purified by silica gel chromatography (20% to 60% EtOAc/hexanes) to afford the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.35-7.25 (m, 5H), 5.44 (d, J=8.4 Hz, 1H), 4.88 (d, J=3.2 Hz, 1H), 4.53 (dd, J=12.4, 28.8 Hz, 2H), 3.71 (s, 3H), 3.69-3.64 (m, 2H), 3.21 (s, 3H), 1.44 (s, 9H). ES MS (M+1−100, for loss of BOC group)=239.2.

Workup

  1. temperatureto warm to ambient temperature
  2. filtrationThe mixture was filtered
  3. washwashing the solid residue with excess CH2Cl2
  4. concentrationthe filtrate was concentrated in vacuo
  5. stirringstirred for 20 min
  6. filtrationfiltered once more
  7. washwashing with EtOAc
  8. concentrationThe filtrate was concentrated to an orange oil which
  9. customwas purified by silica gel chromatography (20% to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-505c3537c9db47c99382f0981cf0130a
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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