4-Methylmorpholine → HCID 21092742, compound

HRID 1348989Notes

Reaction equation

HRID 1348989 reaction equation
[C:1]1([C:7]2[S:11][C:10]([S:12]([NH:15][CH2:16][CH2:17][N:18]([C:23](=[O:34])[CH2:24][N:25]3[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]3=[O:27])[CH2:19][C:20]([OH:22])=O)(=[O:14])=[O:13])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.ClC(OCC(C)C)=O>O1CCCC1>[C:1]1([C:7]2[S:11][C:10]([S:12]([N:15]3[CH2:16][CH2:17][N:18]([C:23](=[O:34])[CH2:24][N:25]4[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]4=[O:27])[CH2:19][C:20]3=[O:22])(=[O:14])=[O:13])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 21092811HCID 21092811, compound

Product 1

HCID 21092742HCID 21092742, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of N-[2-(5-phenyl-1,3,4-thiadiazole-2-sulfonylamino)-ethyl]-N-[(thymin-1-yl)-acetyl]-glycine (1.02 g, 2 mmol) in tetrahydrofuran (50 mL) was added N-methylmorpholine (3.3 mL, 3 mmol) and then the mixture was cooled to −20° C. After stirring for 5 min at the same temperature, isobutyl chloroformate (3.4 mL, 26 mmol) was added to the reaction mixture. The resulting mixture was slowly warmed to 0° C. for 1 hour. Then the reaction mixture was evaporated in vacuo and dissolved in a mixture of ethyl acetate and acetonitrile. The solution was washed with brine and dried over sodium sulfate and filtered. The filtrate was evaporated in vacuo and triturated with tetrahydrofuran-ethyl ether (1/1, v/v) to precipitate solid. The solid was filtered off, washed with ethyl ether, and dried in vacuo to give the titled compound (883 mg, 90%). 1H NMR (500 MHz; DMSO-d6) δ 11.30 (s, 0.6H), 11.29 (s, 0.4H), 8.10 (d, 2H), 7.68–7.57 (m, 3H), 7.33 (s, 0.6H), 7.27 (s, 0.4H), 4.66 (s, 1.2H), 4.58 (s, 0.8H), 4.43 (s, 0.8H), 4.30 (s, 1.2H), 4.17 (t, 1.2H), 4.02 (t, 0.8H), 3.95 (t, 1.2H), 3.85 (t, 0.8H), 1.73(s, 3H).

Workup

  1. additionwas added to the reaction mixture
  2. temperatureThe resulting mixture was slowly warmed to 0° C. for 1 hour
  3. customThen the reaction mixture was evaporated in vacuo
  4. dissolutiondissolved in a mixture of ethyl acetate and acetonitrile
  5. washThe solution was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo
  9. customtriturated with tetrahydrofuran-ethyl ether (1/1
  10. customv/v) to precipitate solid
  11. filtrationThe solid was filtered off
  12. washwashed with ethyl ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-beac9a7ca75a4ff4be50f9a809329ed3
Source dataset
uspto-grants-2007_05
Patent number
US07211668B2

Reaction notes

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