Pyridine → Ethyl 2-(4-(3-chloropropylsulfonamido)-3-fluorophenyl)propanoate

HRID 1842990Notes

Reaction equation

HRID 1842990 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][C:11]=1[F:23].N1C=CC=CC=1>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][C:11]=1[F:23])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 20364696Ethyl 2-(4-amino-3-fluorophenyl)propanoate

Product 1

HCID 86672169Ethyl 2-(4-(3-chloropropylsulfonamido)-3-fluorophenyl)propanoateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloropropanesulfonyl chloride (0.576 mL, 4.73 mmol) was added to a solution of ethyl 2-(4-amino-3-fluorophenyl)propanoate (1 g, 4.735 mmol) and pyridine (0.382 mL, 4.735 mmol) in DCM (18 mL) at 0° C. The reaction mixture was stirred for 1 h, after it was partitioned between DCM (10 mL) and 1N hydrochloric acid (10 mL). The organic phase was separated and dried over magnesium sulfate, filtered and concentrated in vacuo to afford ethyl 2-(4-(3-chloropropylsulfonamido)-3-fluorophenyl)propanoate as an oil (1.5 g).

Workup

  1. customafter it was partitioned between DCM (10 mL) and 1N hydrochloric acid (10 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f64fe9732da4740a36a652f2a5c491d
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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