4-Methylmorpholine → trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

HRID 21968Notes

Reaction equation

HRID 21968 reaction equation
[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16](O)=[O:17])[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2].C[N:21]1CCOCC1.ClC(OCC)=O>O1CCCC1.C(Cl)Cl>[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([NH2:21])=[O:17])[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 86747202trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

Product 1

HCID 86747204trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.30 g, 1.05 mmol) is dissolved in tetrahydrofuran (5.0 mL). 4-Methylmorpholine (0.14 mL, 1.05 mmol) is then added, and the reaction is cooled to -20° C. Ethyl chloroformate (0.1 mL, 1.05 mmol) is then added, and the reaction is stirred at -20° C. for 30 minutes. The reaction is then filtered, and the filtrate is concentrated to give a yellow oil. This oil is dissolved in methylene chloride (20.0 mL), and anhydrous ammonia gas is bubbled through the solution for 1 hour. The bubbling is stopped, and the reaction is stirred an additional 1 hour. The solvent is evaporated, and the residue is partitioned between ethyl acetate and water. The aqueous layer is extracted several times with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated to give trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide, MS: M+1=287.

Workup

  1. filtrationThe reaction is then filtered
  2. concentrationthe filtrate is concentrated
  3. customto give a yellow oil
  4. customanhydrous ammonia gas is bubbled through the solution for 1 hour
  5. stirringthe reaction is stirred an additional 1 hour
  6. customThe solvent is evaporated
  7. customthe residue is partitioned between ethyl acetate and water
  8. extractionThe aqueous layer is extracted several times with ethyl acetate
  9. dry with materialthe combined organic layers are dried (Na2SO4)
  10. customthe solvent is evaporated

Sources & evidence

ORD record
ord-dc383267497f4e0695dcbf04fc46f7bb
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Reaction notes

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