4-Methylmorpholine → HCID 67079724, compound

HRID 655536Notes

Reaction equation

HRID 655536 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][CH2:22][CH2:23][C@H:24]([NH:28][CH2:29][CH:30]([O:33][CH3:34])[O:31][CH3:32])[CH2:25][O:26][CH3:27])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:11](=[O:13])[N:28]([C@H:24]([CH2:25][O:26][CH3:27])[CH2:23][CH2:22][O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:29][CH:30]([O:31][CH3:32])[O:33][CH3:34])[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67080067HCID 67080067, compound

Product 1

HCID 67079724HCID 67079724, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-L-alanine (1.12 g, 5.92 mmol) and ((S)-3-benzyloxy-1-methoxymethyl-propyl)-(2,2-dimethoxy-ethyl)-amine (1.60 g, 5.38 mmol) in N,N-dimethylformamide (16 mL) were added 4-methylmorpholine (1.63 g, 16.1 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (3.07 g, 8.06 mmol) at room temperature. The reaction mixture was stirred at room temperature was stirred at room temperature for 16 h, then partitioned between water and heptane/ethyl acetate 1:1. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) furnished the title compound (2.20 g, 87%). Colorless oil, MS (ISP)=469.4 (M+H)+.

Workup

  1. stirringwas stirred at room temperature for 16 h
  2. custompartitioned between water and heptane/ethyl acetate 1:1
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c746905d0c574cf682f5df581313f173
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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