4-Toluenesulfonyl chloride → HCID 178427793, compound

HRID 707389Notes

Reaction equation

HRID 707389 reaction equation
[OH:1][C@@H:2]1[CH2:5][C@H:4]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:1][C@H:2]2[CH2:3][C@@H:4]([NH:6][C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16])[CH2:5]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178523833HCID 178523833, compound

Product 1

HCID 178427793HCID 178427793, compoundYield 123.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Intermediate 47 (0.67 g, 3.03 mmol), p-toluenesulfonyl chloride (Sigma Aldrich, 1.155 g, 6.06 mmol), triethylamine (Aldrich, 1.688 ml. 12.11 mmol) in DCM (6.06 ml) was stirred at room temperature overnight. Reaction mixture was diluted with DCM and washed with saturated NaHCO3 solution. Organic layer was dried over sodium sulfate to provide 1.4 g crude product upon rotovap. Material was advanced to next step before further purification.

Workup

  1. customReaction mixture
  2. washwashed with saturated NaHCO3 solution
  3. dry with materialOrganic layer was dried over sodium sulfate

Sources & evidence

ORD record
ord-59949fcbbcbc401393beabb8d82feb2f
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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