4-Toluenesulfonyl chloride → HCID 89524914, compound

HRID 1620999Notes

Reaction equation

HRID 1620999 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:18])([CH2:15][CH2:16][OH:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].N12CCCN=C1CCCCC2>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:18])([CH2:15][CH2:16][O:17][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 89524644HCID 89524644, compound

Product 1

HCID 89524914HCID 89524914, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of Example 135C (8.8 g, 30 mmol) in CH2Cl2 was added tosyl chloride (2 equivalents) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.5 equivalents) and the mixture stirred overnight at room temperature. Purification by column chromatography on silica gel provided title compound (3.3 g, 25%).

Workup

  1. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-3df22b5d27054792975a8c5e8318356e
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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