Hydrochloric Acid → Acetic Acid 2-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzenesulfonylamino)-1,1-dimethyl-2-oxo-ethyl Ester

HRID 11666

Reaction equation

HRID 11666 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.C(N(CC)CC)C.Cl[C:40]([C:42]([O:45][C:46](=[O:48])[CH3:47])([CH3:44])[CH3:43])=[O:41].Cl>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[C:6]([S:8]([NH:11][C:40](=[O:41])[C:42]([O:45][C:46](=[O:48])[CH3:47])([CH3:44])[CH3:43])(=[O:9])=[O:10])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 692957585-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzenesulfonamide

Product 1

HCID 69655351Acetic Acid 2-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzenesulfonylamino)-1,1-dimethyl-2-oxo-ethyl EsterYield 111.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzenesulfonamide (0.10 g, 0.21 mmol) in dichloromethane (2 mL) was added triethylamine (0.033 mL, 0.23 mmol), 4-dimethylaminopyridine (5 mg, 0.04 mmol) and acetic acid 1-chlorocarbonyl-1-methyl-ethyl ester (0.037 mL, 0.25 mmol). The resulting reaction mixture was stirred at ambient temperature overnight, treated with 0.2 N hydrochloric acid extracted with dichloromethane dried over magnesium sulfate, filtered and concentrated in vacuo to give the crude title compound (0.140 g).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c8d94f9fb99434eb3bbcfd9034a6337
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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