Oxalyl chloride → HCID 178483791, compound

HRID 2118236Notes

Reaction equation

HRID 2118236 reaction equation
[CH3:1][N:2]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=O)[CH2:5][CH2:4]1.C(Cl)(=O)C(Cl)=O.[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][NH:35][CH3:36]>C(Cl)Cl.CN(C=O)C>[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][N:35]([CH3:36])[C:9]([C@H:6]1[CH2:5][CH2:4][C@H:3]([N:2]([CH3:1])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][CH:16]=2)(=[O:13])=[O:14])[CH2:8][CH2:7]1)=[O:11]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 178484815HCID 178484815, compound

Product 1

HCID 178483791HCID 178483791, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.137 g (0.375 mmol) of trans-4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexanecarboxylic acid in 2 mL of CH2Cl2 was treated at RT with 1 drop of DMF, followed by 0.035 mL (0.412 mmol, 1.1 eq) of oxalyl chloride within 5 min, and stirring was continued for 90 min. The solution was evaporated, redissolved in 2 mL of CH2Cl2 and treated with 0.058 mL (0.450 mmol, 1.2 eq) of N,N,N′-trimethylethylenediamine at 0° C. The reaction was kept at RT for 2 h, then partitioned between Et2O (×3)/aqueous saturated NaHCO3. The organic phases were washed once with 10% aqueous NaCl, dried over Na2SO4 and evaporated. Purification by flash-chromatography on 8 g of silica gel (CH2Cl2:MeOH 99:1 to 9:1) gave 0.088 g (53%) of pure trans-4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexanecarboxylic acid (2-dimethylamino-ethyl)-methyl-amide, MS: 450 (MH+), MP: 83° C.

Workup

  1. customThe solution was evaporated
  2. dissolutionredissolved in 2 mL of CH2Cl2
  3. waitThe reaction was kept at RT for 2 h
  4. custompartitioned between Et2O (×3)/aqueous saturated NaHCO3
  5. washThe organic phases were washed once with 10% aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customPurification by flash-chromatography on 8 g of silica gel (CH2Cl2:MeOH 99:1 to 9:1)

Sources & evidence

ORD record
ord-c9605360ea4543a29c28e69b32155622
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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