3-Chloro-4-fluorobenzenesulphonyl chloride → HCID 59192544, compound

HRID 1696881Notes

Reaction equation

HRID 1696881 reaction equation
Cl.[C:2]([O:6][C:7](=[O:21])[CH2:8][O:9][C:10]1[C:19]2[CH2:18][CH2:17][CH2:16][C@@H:15]([NH2:20])[C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:5])([CH3:4])[CH3:3].[Cl:22][C:23]1[CH:24]=[C:25]([S:30](Cl)(=[O:32])=[O:31])[CH:26]=[CH:27][C:28]=1[F:29]>CN(C)C1C=CN=CC=1.O1CCCC1>[C:2]([O:6][C:7](=[O:21])[CH2:8][O:9][C:10]1[C:19]2[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:20][S:30]([C:25]3[CH:26]=[CH:27][C:28]([F:29])=[C:23]([Cl:22])[CH:24]=3)(=[O:32])=[O:31])[C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 67183783HCID 67183783, compound

Product 1

HCID 59192544HCID 59192544, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of dimethyl-pyridin-4-yl-amine (1.17 g, 9.60 mmol) in tetrahydrofuran (10 mL) was added dropwise to a solution of (R)-(5-amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester hydrochloride salt (1 g, 3.18 mmol) and 3-chloro-4-fluoro-benzenesulfonyl chloride (0.68 mL, 4.77 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature overnight, and then concentrated. The residue was purified by column chromatography (gradient elution, 0-5% methanol in dichloromethane) to afford (R)-[5-(3-chloro-4-fluoro-benzenesulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester (1.4 g, 93.8%) as a white solid. MS calcd. for C22H25ClFNO5S 469, obsd 470 (ESI+) [(M+H)+].

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography (gradient elution, 0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e34b84bf6fc6448da9158417fa2ff445
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

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