4-(Propan-2-yl)benzene-1-sulfonyl chloride → HCID 68916925, compound

HRID 870346Notes

Reaction equation

HRID 870346 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C@@H:8]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:9]2)=[CH:4][CH:3]=1.[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]>N1C=CC=CC=1.ClCCl>[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][C@@H:8]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:9]3)=[CH:4][CH:3]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 68912619HCID 68912619, compound

Product 1

HCID 68916925HCID 68916925, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Conditions

Temperature
5 °C

Procedure

(R)—N-(7-Amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-propionamide (0.34 g, 1.56 mmol) was dissolved in pyridine-dichloromethane (1:2, 30 mL) and cooled to 5° C. 4-Isopropylbenzenesulfonyl chloride (0.37 g, 1.69 mmol) was added and the solution stirred at 5° C. for 3 h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated to give the product as a yellow oil (0.56 g, 90%).

Workup

  1. customSolution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. customthe organic phase separated
  4. dry with materialdried over MgSO4
  5. concentrationThe filtered solution was concentrated

Sources & evidence

ORD record
ord-9ed1e8568ab5406eba03eb7098aafd4d
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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