Methanesulfonyl chloride → HCID 58786412, compound

HRID 1376041Notes

Reaction equation

HRID 1376041 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][NH:16][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 587864641,1-Dimethylethyl 4-[2-amino-1-(2-fluorophenyl)ethyl]-1-piperazinecarboxylate

Product 1

HCID 58786412HCID 58786412, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[2-Amino-1-(2fluoro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (207) (0.71 g, 2.19 mmol) in THF (5 mL) at 0° C. was added diisopropylethylamine (0.42 mL, 2.42 mmol). The solution was allowed to stir for 10 min. Methansulfonyl chloride (0.17 mL, 2.19 mmol) was then added and the solution was allowed to stir at room temperature for 18 h. The reaction mixture was diluted with EtOAc (50 mL) and washed with brine (50 mL) and H2O (50 mL). The organic phase was concentrated to dryness yielding 0.86 g (98%) product.

Workup

  1. stirringto stir at room temperature for 18 h
  2. washwashed with brine (50 mL) and H2O (50 mL)
  3. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-9c9b8a3ace3247218fccfc3a8f15bd8b
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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