Phenylmethanesulfonyl chloride → HCID 178501526, compound

HRID 840791Notes

Reaction equation

HRID 840791 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C@@H:7]([CH2:11][CH2:12][C:13]([NH:15][CH2:16][NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[NH:14])[C:6]1=[O:28].CCN(C(C)C)C(C)C.[C:39]1([CH2:45][S:46](Cl)(=[O:48])=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:29])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([S:46]([CH2:45][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:48])=[O:47])[C@@H:7]([CH2:11][CH2:12][C:13]([NH:15][CH2:16][NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[NH:14])[C:6]1=[O:28]

Participants

5

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178501524HCID 178501524, compound

Product 1

HCID 178501526HCID 178501526, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the compound of Example 16 (0.48 mmol) and DIEA in CH2Cl2 (2 mL) at −78° C., was added α-toluenesulfonyl chloride (110 mg, 0.57 mmol). The mixture was stirred at −78° C. for three hours and evaporated in vacuo. The residue was dissolved in CH2Cl2 and H2O. The organic layer was washed with sat. NaHCO3, sat. NaCl, dried over Na2SO4 and evaporated to give the title compound as a solid (50% yield).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washThe organic layer was washed with sat. NaHCO3, sat. NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-e4372551e47d4cd1b1c50f53e7cc35d6
Source dataset
uspto-grants-2002_04
Patent number
US06369063B1

Reaction notes

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