Triethylamine → HCID 86640101, compound

HRID 555364Notes

Reaction equation

HRID 555364 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][CH2:10]/[C:11](/[CH2:20][O:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.[O:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[O:50][NH2:51].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][CH2:10]/[C:11](/[CH2:20][O:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:51][O:50][CH:45]2[CH2:46][CH2:47][CH2:48][CH2:49][O:44]2)=[O:18])[CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 66987279HCID 66987279, compound

Product 1

HCID 86640101HCID 86640101, compoundYield 43%

Procedure

(Z)-8-(2-morpholinoethylamino)-7-((naphthalen-1-yloxy)methyl)oct-6-enoic acid (268 mg, 0.63 mmol) obtained in Example (3-1-2) was dissolved in N,N′-dimethylformal (3.2 ml) in a 25 ml vessel, and to the resulting mixture, N-hydroxy-6-trifluorobenzotriazole (FOBt; 140 mg, 0.69 mmol, 1.1 eq.), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl; 157 mg, 0.82 mmol, 1.3 eq.), tetrahydro-2H-pyran-2-yloxyamine (THPONH2; 111 mg, 0.95 mmol, 1.5 eq.), and triethylamine (0.18 ml, 1.26 mmol, 1.5 eq.) were added at 0° C., while stirring. The resulting mixture was heated to room temperature and stirred for 12 hrs. After the completion of reaction, 10% aqueous potassium carbonate solution was added to the reaction mixture, and then the resultant was extracted with ethyl acetate. The organic layer was separated, washed with an aqueous saturated sodium bicarbonate solution and brine in order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 142 mg of the title compound as dark yellow foam (yield 43%).

Workup

  1. stirringstirred for 12 hrs
  2. additionwas added to the reaction mixture
  3. extractionthe resultant was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with an aqueous saturated sodium bicarbonate solution and brine in order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-94392f8cd7f1471887ea470fe04e31a4
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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