4-Methylmorpholine → HCID 58813137, compound

HRID 1391714Notes

Reaction equation

HRID 1391714 reaction equation
CN1CCOCC1.Cl.[NH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].[CH2:15]([C@@H:19]([CH2:23][CH:24]=[CH2:25])[C:20](O)=[O:21])[CH:16]([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[CH2:15]([C@@H:19]([CH2:23][CH:24]=[CH2:25])[C:20]([NH:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:21])[CH:16]([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 122755Glycine methyl ester hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58813142HCID 58813142, compound

Product 1

HCID 58813137HCID 58813137, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Step M (1): NMM (11.0 mL, 100 mmol) was added to a mixture of methyl 2-aminoacetate hydrochloride (4.44 g, 35.3 mmol), (S)-2-isobutylpent-4-enoic acid [prepared as described in WO 2004/013098] (4.6 g, 29.5 mmol), HATU (13.4 g, 35.3 mmol in DCM (200 mL) at room temperature. The mixture was stirred for 16 h. Poured the reaction mixture into 150 mL H2O. Extracted with DCM (3×250 mL). Washed combined organic extracts with brine, dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give (S)-methyl 2-(2-isobutylpent-4-enamido)acetate 4.0 g (60% yield) as a colorless oil: ESI (M+H)+=228.22. 1H NMR (300 MHz, CDCl3) δ ppm 0.79-0.93 (m, 6H) 1.15-1.30 (m, 1H) 1.48-1.71 (m, 2H) 2.08-2.38 (m, 3H) 3.72 (s, 3H) 4.01 (d, J=5.12 Hz, 2H) 4.92-5.09 (m, 2H) 5.63-5.78 (m, 1H) 5.92 (s, 1H).

Workup

  1. extractionExtracted with DCM (3×250 mL)
  2. washWashed
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2bcd5668a7c42749dfc9ab3d73514af
Source dataset
uspto-grants-2008_03
Patent number
US07338974B2

Reaction notes

Loading…