Sodium Iodide → HCID 178464459, compound

HRID 25639Notes

Reaction equation

HRID 25639 reaction equation
[CH3:1][N:2]([C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)=[O:18])[C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][CH2:10]COS(C)(=O)=O)[CH2:5][CH2:4]1.[CH2:30]([NH:32][CH2:33][CH2:34][OH:35])[CH3:31].[Na+].[I-].[CH3:38]C(N(C)C)=O>>[F:27][C:26]([F:28])([F:29])[C:23]1[CH:24]=[CH:25][C:20]([O:19][C:17](=[O:18])[N:2]([C@H:3]2[CH2:8][CH2:7][C@H:6]([CH2:9][CH2:10][CH2:38][N:32]([CH2:30][CH3:31])[CH2:33][CH2:34][OH:35])[CH2:5][CH2:4]2)[CH3:1])=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 80722-(Ethylamino)ethanol3×HCID 31374DimethylacetamideHCID 178485958HCID 178485958, compound

Product 1

HCID 178464459HCID 178464459, compoundYield 22%

Procedure

A solution of 293 mg (corresponds to 0.5 mmol) of trans-Methanesulfonic acid 3-{4-[methyl-(4-trifluoromethyl-phenoxycarbonyl)-amino]-cyclohexyl}-propyl ester in 2.5 ml of DMA was cooled to 0° C., treated with 0.195 ml (2 mmol) of Ethyl-(2-hydroxy-ethyl)-amine and stirred over night at RT. A catalytic amount of NaI and 0.195 ml (2 mmol) of Ethyl-(2-hydroxy-ethyl)-amine and after 9 h, 0.88 ml (1 mmol) of Ethyl-(2-hydroxy-ethyl)-amine were added. After 16 h, the solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried with Na2SO4, filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 9:1) gave 48 mg (22%) of pure trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-methyl-carbamic acid 4-trifluoromethyl-phenyl ester, MS: 431 (MH+). The following compounds were prepared in analogy:

Workup

  1. customthe solvent was evaporated
  2. extractionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-08c39b2c5b2d4ecd804296a5e6ab6fff
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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