Iodopentafluoroethane → HCID 57086944, compound

HRID 2258495Notes

Reaction equation

HRID 2258495 reaction equation
COCN[C:5]([CH:7]1[CH2:11][S:10][CH2:9][N:8]1[C:12]([CH:14]1[CH2:18][S:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:13])=[O:6].[F:26][C:27](I)([F:32])[C:28]([F:31])([F:30])[F:29].C[Li].[Br-].[Li+]>C(OCC)C>[F:26][C:27]([F:32])([C:28]([F:31])([F:30])[F:29])[C:5]([CH:7]1[CH2:11][S:10][CH2:9][N:8]1[C:12]([CH:14]1[CH2:18][S:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:13])=[O:6]

Participants

6

Reactant 4

HCID 9636IodopentafluoroethaneHCID 82050Lithium BromideHCID 57033220HCID 57033220, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 57086944HCID 57086944, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a stirred solution of 4-[[4-[(methoxymethylamino)carbonyl]-3-thiazolidinyl]carbonyl]-3-thiazolidine carboxylic acid, 1,1-dimethylethyl ester (compound from Example IIID; 0.33 g, 0.84 mmol) in ethyl ether (30 ml) under argon at -78° C. was added perfluoroethyl iodide (0.32 ml, 2.70 mmol) followed by methyl lithium.lithium bromide (1.57 ml, 2.36 mmol, 1.5M in ethyl ether). TLC indicated the reaction was complete. The reaction was poured into 100 ml ethyl ether containing 25 g silica gel. Residual amounts of product in the flask were dissolved in ethyl ether and added to the silica/ether solution. Subsequently, the organic phase was removed and the silica gel was washed with ethyl ether (2×100 ml). The combined organics were dried over magnesium and sodium sulfate and then filtered and evaporated to give an oily white foam (0.34 g). The material was then flash chromatographed on a 4×10 cm silica gel column eluting with 0.4 liter of ethyl acetate/hexane (30:70) followed by 0.5 liter of ethyl acetate/hexane (75:25). Product containing fractions were combined and concentrated to an oil (49 mg).

Workup

  1. customat -78° C.
  2. additionadded to the silica/ether solution
  3. customSubsequently, the organic phase was removed
  4. washthe silica gel was washed with ethyl ether (2×100 ml)
  5. dry with materialThe combined organics were dried over magnesium and sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d71b1bef74184d789d0688d950b26595
Source dataset
uspto-grants-1997_08
Patent number
US05661167

Reaction notes

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