4-Methylmorpholine → HCID 69317107, compound

HRID 1391712Notes

Reaction equation

HRID 1391712 reaction equation
CN1CCOCC1.Cl.[NH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].[CH2:15]([O:22][C:23]([NH:25][C@:26]([CH:33]([CH2:35][CH3:36])[CH3:34])([CH2:30][CH:31]=[CH2:32])[C:27](O)=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[CH2:15]([O:22][C:23]([NH:25][C@:26]([CH:33]([CH2:35][CH3:36])[CH3:34])([CH2:30][CH:31]=[CH2:32])[C:27]([NH:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

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 69317597HCID 69317597, compound

Product 1

HCID 69317107HCID 69317107, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Step L (1): NMM (9.8 mL, 89.1 mmol) was added to a mixture of methyl 2-aminoacetate hydrochloride (3.95 g, 31.4 mmol), (2S)-2-(benzyloxycarbonyl-amino)-2-sec-butylpent-4-enoic acid (8.0 g, 26.2 mmol) [prepared as described in WO 2004/013098] HATU (12 g, 31.4 mmol in DCM (300 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 methyl 2-((2S)-2-(benzyloxycarbonylamino)-2-sec-butylpent-4-enamido)acetate 9.8 g (99% yield) as a yellow-oily residue: ESI (M+H)+=377.43. 1H NMR (300 MHz, CDCl3) δ ppm 0.93-1.08 (m, 6H) 1.49-1.56 (m, 3H) 2.74-2.89 (m, 2H) 3.68 (s, 3H) 4.10-3.96 (m, 2H) 5.00-5.22 (m, 4H) 5.85-5.94 (m, 1H) 7.33-7.40 (m, 5H).

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-1902cbd6b7fa41f68087ed991e2ea4fc
Source dataset
uspto-grants-2008_03
Patent number
US07338974B2

Reaction notes

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