4-Methylmorpholine → HCID 53240755, compound

HRID 422176Notes

Reaction equation

HRID 422176 reaction equation
[CH3:1][C@@:2]12[CH2:19][CH2:18][C@@H:17]3[C@:12]([CH3:22])([CH2:13][CH2:14][CH2:15][C:16]3([CH3:21])[CH3:20])[C@H:11]1[CH2:10][S:9](=[O:24])(=[O:23])[C:8]1[C:3]2=[C:4]([C:28]([OH:30])=O)[CH:5]=[C:6]([C:25](O)=[O:26])[CH:7]=1.[CH3:31][N:32](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:55][N:56]1CCOCC1>C1COCC1.CN(C=O)C>[CH3:1][C@@:2]12[CH2:19][CH2:18][C@@H:17]3[C@:12]([CH3:22])([CH2:13][CH2:14][CH2:15][C:16]3([CH3:21])[CH3:20])[C@H:11]1[CH2:10][S:9](=[O:24])(=[O:23])[C:8]1[C:3]2=[C:4]([C:28]([NH:56][CH3:55])=[O:30])[CH:5]=[C:6]([C:25]([NH:32][CH3:31])=[O:26])[CH:7]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53240754HCID 53240754, compound

Product 1

HCID 53240755HCID 53240755, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3,5-dicarboxylic acid (85) (0.07 g, 0.2 mmol), HATU (0.25 g, 0.65 mmol) and 4-methylmorpholine (0.07 mL, 1 mmol) in THF (10 mL) and DMF (2.0 mL) was stirred at room temperature for 18 h in a sealed vessel. The mixture was concentrated under reduced pressure and the residue was triturated with water. The resulting solid was collected by filtration to give (1R,10R,11S,16S)-1,3-N,5-N,11,15,15-hexamethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3,5-dicarboxamide (86) (0.035 g, 47%) as a white solid. 1H NMR (CD3OD): δ 8.38 (d, 1H), 7.88 (d, 1H), 3.54 (m, 2H), 2.90 (d, 6H), 2.67 (d, 1H), 2.18 (d, 1H), 1.90-1.48 (m, 9H), 1.46-1.14 (m, 3H), 1.06-0.93 (m, 4H), 0.90 (s, 3H), 0.87 (s, 3H). MS m/z 461 (C25H36N2O4S+H+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was triturated with water
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-32fa8ad951f7428586a61fe7209cd6ce
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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