4-Methylmorpholine → thioacetic acid S-[3-benzylsulfanyl-2-(cyanomethyl-carbamoyl)-propyl]ester

HRID 1830167Notes

Reaction equation

HRID 1830167 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:10][S:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].C1C=[C:23]2[N:25]=N[N:27](O)[C:22]2=CC=1.O.Cl.NCC#N.CN1CCOCC1>C(OCC)(=O)C.C(Cl)Cl.C(Cl)CCl>[CH2:12]([S:11][CH2:10][CH:6]([C:7](=[O:9])[NH:27][CH2:22][C:23]#[N:25])[CH2:5][S:4][C:1](=[O:3])[CH3:2])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 11491918Aminoacetonitrile hydrochlorideHCID 220539433-Acetylsulfanyl-2-benzylsulfanylmethyl-propionic acid

Product 1

HCID 86611134thioacetic acid S-[3-benzylsulfanyl-2-(cyanomethyl-carbamoyl)-propyl]esterYield 96.1%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-acetylsulfanyl-2-benzylsulfanylmethyl-propionic acid (0.200 g), prepared as in Reference 10, HOBt hydrate (0.13 g), aminoacetonitrile hydrochloride (0.15 g) and EDC (0.26 g) was treated with methylene chloride (6 mL) and N-methylmorpholine (0.35 mL). After stirring for 80 minutes at room temperature, the reaction mixture was diluted with ethyl acetate (50 mL) and washed sequentially with water, aqueous sodium bicarbonate and saturated aqueous sodium chloride. The solution was dried over magnesium sulfate and evaporated to give thioacetic acid S-[3-benzylsulfanyl-2-(cyanomethyl-carbamoyl)-propyl] ester (0.218 g).

Workup

  1. washwashed sequentially with water, aqueous sodium bicarbonate and saturated aqueous sodium chloride
  2. dry with materialThe solution was dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-5a12a0f757a946e3a843837529e21e90
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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