Potassium Carbonate → HCID 14328281, compound

HRID 330072Notes

Reaction equation

HRID 330072 reaction equation
[C:1](Cl)(=[O:6])[C:2](C)(C)C.C(O[O:12][C:13]1[C:22]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:21][C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]=1)(=O)C.Cl.[Cl:31][CH2:32][CH2:33][NH2:34].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(N(CC)CC)C.C(Cl)(Cl)Cl>[Cl:31][CH2:32][CH2:33][NH:34][C:1](=[O:6])[CH2:2][O:12][C:13]1[C:22]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:21][C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 62493Pivaloyl chlorideHCID 97937372-Chloroethylamine hydrochlorideHCID 86743690HCID 86743690, compound

Product 1

HCID 14328281HCID 14328281, compoundYield 79.5%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

Pivaloyl chloride (3.05 g, 25 mM) was added dropwise at -5° C. to compound 660 (7.45 g, 25 mM) and triethylamine (3.5 ml, 25 mM) dissolved in tetrahydrofuran (45 ml), then the mixture was stirred for 30 minutes. Chloroform (25 ml) in solution with 2-chloroethylamine hydrochloride (2.90 g) and triethylamine (3.5 ml) was added dropwise thereto, then the mixture was stirred for 1 hour with ice cooling and 4 hours at room temperature. Dilute aqueous potassium carbonate was added to the reaction mixture and the mixture was extracted twice with chloroform. The extract was dried with anhydrous sodium sulfate, and concentrated in vacuo. The residue was charged on a column of silica gel (C-200, 175 g) and eluted successively with benzene and benzene-ethyl acetate to obtain the product. (7.142 g, yield: 79.5%).

Workup

  1. stirringthe mixture was stirred for 1 hour with ice cooling and 4 hours at room temperature
  2. extractionthe mixture was extracted twice with chloroform
  3. dry with materialThe extract was dried with anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. additionThe residue was charged on a column of silica gel (C-200, 175 g)
  6. washeluted successively with benzene and benzene-ethyl acetate
  7. customto obtain the product

Sources & evidence

ORD record
ord-1180b172925446af8d94639a924ae06e
Source dataset
uspto-grants-1990_01
Patent number
US04894453

Reaction notes

Loading…