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Sodium Carbonate → Methyl 1-[4-(2-nitrobenzenesulfonyl)-piperazin-1-yl]-cyclopropanecarboxylate

HRID 1361431
Notes
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Reaction equation

HRID 1361431 reaction equation
FC(F)(F)S(O[CH2:7][CH2:8][N:9]([CH2:22][CH2:23]OS(C(F)(F)F)(=O)=O)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])(=O)=O.Cl.[NH2:35][C:36]1([C:39]([O:41][CH3:42])=[O:40])[CH2:38][CH2:37]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([N:9]1[CH2:8][CH2:7][N:35]([C:36]2([C:39]([O:41][CH3:42])=[O:40])[CH2:38][CH2:37]2)[CH2:23][CH2:22]1)(=[O:11])=[O:12])([O-:21])=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 12760695Methyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 86601384N,N-Bis-(2-trifluoromethanesulfonyloxyethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 66628127Methyl 1-[4-(2-nitrobenzenesulfonyl)-piperazin-1-yl]-cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 6342
Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N,N-bis-(2-trifluoromethanesulfonyloxyethyl)-2-nitrobenzenesulfonamide (1.83 g, 3.30 mmol) from Example 16B and methyl 1-aminocyclopropane-1-carboxylate HCl (0.50 g, 3.30 mmol) in anhydrous acetonitrile (10 mL) was treated with sodium carbonate (1.40 g, 13.2 mmol) and heated overnight at 60° C. (J. A. Kozlowski, et al., Bioorg. Med. Chem. Lett. 12: 791-794, 2002). Reaction diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column eluting with 3:1 hexane:ethyl acetate to afford the title compound. MS(ESI) m/z 370 (M+H)+.

Workup

  1. customReaction
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column
  7. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-1999be03e6f24a4494afcf18cea27a46
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07880001B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes