Triethylamine → HCID 59676768, compound

HRID 902899Notes

Reaction equation

HRID 902899 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:19][NH:18][CH2:17][C@H:16]1[NH:20][C:21]([C:23]1[S:24][C:25]3[CH2:26][N:27]([CH3:32])[CH2:28][CH2:29][C:30]=3[N:31]=1)=[O:22])=[O:13])=[CH:6]2.C(N(CC)CC)C.[CH3:40][O:41][C:42]([CH2:44][S:45](Cl)(=[O:47])=[O:46])=[O:43]>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@H:15]1[C@H:16]([NH:20][C:21]([C:23]3[S:24][C:25]4[CH2:26][N:27]([CH3:32])[CH2:28][CH2:29][C:30]=4[N:31]=3)=[O:22])[CH2:17][N:18]([S:45]([CH2:44][C:42]([O:41][CH3:40])=[O:43])(=[O:47])=[O:46])[CH2:19]1)=[O:13])=[CH:6]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11435213Methyl (chlorosulfonyl)acetateHCID 67056761HCID 67056761, compound

Product 1

HCID 59676768HCID 59676768, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (230 mg) obtained in Example 95 and triethylamine (0.10 ml) were dissolved in methylene chloride (6.9 ml), and the mixture was cooled with ice. Methoxycarbonylmethanesulfonyl chloride (Synthesis, p. 321, 1975) (105 mg) was added, and the resultant mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with chloroform, washed with water and saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by preparative thin-layer chromatography on silica gel (chloroform:methanol=20:1) and powdered with methanol-water to obtain the title compound (150 mg).

Workup

  1. temperaturethe mixture was cooled with ice
  2. washwashed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by preparative thin-layer chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-f57b58ab133640c1b68496cd4ce11858
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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