4-Methylmorpholine → HCID 68520987, compound

HRID 644947Notes

Reaction equation

HRID 644947 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]2[C:14]([OH:16])=O)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[Cl-].[CH:47]1([C:53]2([CH2:59][N:60]3[C:64]([CH3:66])([CH3:65])[CH2:63][O:62][C:61]3=[O:67])[CH2:58][CH2:57][NH2+:56][CH2:55][CH2:54]2)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]2[C:14]([N:56]2[CH2:57][CH2:58][C:53]([CH2:59][N:60]3[C:64]([CH3:65])([CH3:66])[CH2:63][O:62][C:61]3=[O:67])([CH:47]3[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]3)[CH2:54][CH2:55]2)=[O:16])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17980475HCID 17980475, compoundHCID 68519009HCID 68519009, compound

Product 1

HCID 68520987HCID 68520987, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL round bottom flask equipped with a magnetic stir bar was charged with 0.285 g (1.18 mmol) of the product of Step E dissolved in 4 mL of methylene chloride. To the reaction mixture was added 0.340 g (1.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.240 g (1.78 mmol) of 1-hydroxybenzotriazole, 0.390 μL (3.55 mmol) of N-methylmorpholine, followed by 0.431 g (1.30 mmol) of 4-cyclohexyl-4-[(4,4-dimethyl-2-oxo -1,3-oxazolidin-3-yl)methyl]piperidinium chloride. The resulting solution was stirred at room temperature for 48 h, then was partitioned between methylene chloride and saturated aqueous sodium bicarbonate. The organic layer was separated, washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, brine, dried (Na2SO4), filtered and evaporated in vacuo. The residual amorphous solid was used directly in the next step without further purification.

Workup

  1. customA 25 mL round bottom flask equipped with a magnetic stir bar
  2. customwas partitioned between methylene chloride and saturated aqueous sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residual amorphous solid was used directly in the next step without further purification

Sources & evidence

ORD record
ord-0c4f7c86aa4045c98a53b4d16e7c7187
Source dataset
uspto-grants-2010_04
Patent number
US07700778B2

Reaction notes

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