Triethylamine → HCID 178501351, compound

HRID 1728479Notes

Reaction equation

HRID 1728479 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[N:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:4].C(N(CC)CC)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[N:8]([S:45]([CH3:44])(=[O:47])=[O:46])[C:7](=[O:9])[C@H:6]1[CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[N:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178501360HCID 178501360, compound

Product 1

HCID 178501351HCID 178501351, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a vigorously stirred methylene chloride (10 mL) solution of compound 7 (0.8 g, 1.6 mmol) and triethylamine (4.86 g, 48 mmol ) was added methanesulfonyl chloride (5.52 g, 48 mmol) dropwise. The reaction mixture was diluted with additional CH2Cl2 and washed with pH 7.0 aqueous buffer. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (CH2Cl2 : MeOH/99:1) to afford 340 mg (37%) of the title compound.

Workup

  1. washwashed with pH 7.0 aqueous buffer
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (CH2Cl2 : MeOH/99:1)

Sources & evidence

ORD record
ord-688bf4d3c6fc47e7be5504e0c51473c9
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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