Diisopropylethylamine → 4-[[4-(2,6-Dichlorophenyl)-1,2,5-thiadiazol-3-yl]oxycarbonyl-methyl-amino]butanoic acid

HRID 617445Notes

Reaction equation

HRID 617445 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([OH:14])=[N:12][S:11][N:10]=1.[C:15](=O)(OC(Cl)(Cl)Cl)[O:16]C(Cl)(Cl)Cl.Cl.[CH3:28][NH:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34].C(N(CC)C(C)C)(C)C>ClCCl.O.N1C=CC=CC=1>[CH3:28][N:29]([C:15]([O:14][C:13]1[C:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[N:10][S:11][N:12]=1)=[O:16])[CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 126266544-(Methylamino)butyric acid hydrochlorideHCID 178519022HCID 178519022, compound

Product 1

HCID 4773314-[[4-(2,6-Dichlorophenyl)-1,2,5-thiadiazol-3-yl]oxycarbonyl-methyl-amino]butanoic acidYield 184.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In 10 mL of dichloromethane, were dissolved 490 mg of 3-(2,6-dichlorophenyl)-4-hydroxy-1,2,5-thiadiazole, and 210 mg of bis(trichloromethyl) carbonate. Thereto, 170 mg of pyridine was added. The mixture was stirred at room temperature for 12 hours. Thereto, 340 mg of 4-(methylamino)butyric acid hydrochloride, and 570 mg of N,N-diisopropylethylamine were added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into water, and was extracted with dichloromethane. The dichloromethane layer was washed with dilute hydrochloric acid, and water successively, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography to obtain 510 mg of N-(3-carboxypropyl)-N-methyl [3-(2,6-dichlorophenyl)-1,2,5-thiadiazol-4-yl] carbamate.

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. extractionwas extracted with dichloromethane
  3. washThe dichloromethane layer was washed with dilute hydrochloric acid, and water successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-86a71c6fff594f24af3a8386d140d4f2
Source dataset
uspto-grants-1999_09
Patent number
US05948916

Reaction notes

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