Potassium Carbonate → Sulfuric acid mono-{(R)-1-chloromethyl-2-[4-(3-oxo-morpholin-4-yl)-phenylamino]-ethyl}ester potassium salt

HRID 1506824Notes

Reaction equation

HRID 1506824 reaction equation
[Cl:1][CH2:2][C@H:3]1[CH2:7][O:6][S:5](=[O:9])(=[O:8])[O:4]1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C:18]2=[O:23])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+:28].[K+]>C(#N)C>[K+:28].[Cl:1][CH2:2][C@H:3]([O:4][S:5](=[O:9])(=[O:8])[O-:6])[CH2:7][NH:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C:18]2=[O:23])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 42625092(R)-4-chloromethyl-[1,3,2]dioxathiolane 2,2-dioxide

Product 1

HCID 131734365Sulfuric acid mono-{(R)-1-chloromethyl-2-[4-(3-oxo-morpholin-4-yl)-phenylamino]-ethyl}ester potassium saltYield 126.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under an atmosphere of nitrogen to a solution of a 7.11 g of (R)-4-chloromethyl-[1,3,2]dioxathiolane 2,2-dioxide (MW=156.59; 1.38 eq.) in 95 mL of acetonitrile were added 6.34 g of 4-(4-aminophenyl)-morpholin-3-one (APMO) (MW=192.22; 1 eq.) and 3.29 g (MW=138.21; 0.72 eq.) of potassium carbonate. The reaction mixture was stirred for 24 h at room temperature. Then the resulting suspension was cooled to 0° C. After stirring for at least 2 h at this temperature, the product was isolated by filtration and the filter cake was washed with 50 mL of acetonitrile. After drying in vacuo at 30° C., 12.09 g of the crystalline title compound (MW=402.90) were isolated. Yield=91.0%.

Workup

  1. temperatureThen the resulting suspension was cooled to 0° C
  2. stirringAfter stirring for at least 2 h at this temperature
  3. customthe product was isolated by filtration
  4. washthe filter cake was washed with 50 mL of acetonitrile
  5. customAfter drying in vacuo at 30° C.

Sources & evidence

ORD record
ord-61610dc613b649acbb6e8f1fd3b6436d
Source dataset
uspto-grants-2015_12
Patent number
US09221771B2

Reaction notes

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