Triethylamine → HCID 59676768, compound

HRID 2104453Notes

Reaction equation

HRID 2104453 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. The temperature of the resultant mixture was returned to room temperature, and the mixture was stirred overnight. The reaction mixture was diluted with chloroform, washed with water and saturated brine and then dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1) and powdered with methanol-water to give the title compound (150 mg).

Workup

  1. temperaturethe mixture was cooled with ice
  2. customwas returned to room temperature
  3. washwashed with water and saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resultant residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-68cad706609546e4a0c8f289f46ab21d
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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