Methanesulfonyl chloride → Tert-butyl 1-(4-chlorophenyl)-2-(methylsulfonamido)ethylcarbamate

HRID 423088Notes

Reaction equation

HRID 423088 reaction equation
[NH2:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.C(N(C(C)C)C(C)C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C1COCC1>[Cl:10][C:7]1[CH:6]=[CH:5][C:4]([CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:2][NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57750386tert-butyl N-[2-amino-1-(4-chlorophenyl)ethyl]carbamate2×

Product 1

HCID 57750380Tert-butyl 1-(4-chlorophenyl)-2-(methylsulfonamido)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-amino-1-(4-chlorophenyl)ethylcarbamate (Intermediate 73) (220 mg, 0.81 mmol) and N-ethyldiisopropylamine (0.281 mL, 1.63 mmol) in THF (5 mL) was treated with methanesulfonyl chloride (0.075 mL, 0.98 mmol). The resulting solution was stirred at ambient temperature for 2 hours. The mixture was partitioned between DCM and sodium bicarbonate solution. The organic layer was concentrated and the residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 30% ethyl acetate/DCM). The desired product, tert-butyl 1-(4-chlorophenyl)-2-(methylsulfonamido)ethylcarbamate, was thus isolated as a colourless solid (154 mg, 54.3%).

Workup

  1. customThe mixture was partitioned between DCM and sodium bicarbonate solution
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 30% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-3308806f7f1c40d19db2c5a3af54acf2
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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