1,2,3,4,5-Pentafluoro-6-pentafluorophenoxybenzene → HCID 178454177, compound

HRID 1388866Notes

Reaction equation

HRID 1388866 reaction equation
FC1C(OC2C(F)=C(F)C(F)=C(F)C=2F)=C(F)C(F)=C(F)C=1F.[C:24]([O:28][C:29]([NH:31][C@H:32]([C:48]([OH:50])=O)[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])=[O:30])([CH3:27])([CH3:26])[CH3:25].[NH:51]1[CH2:69][CH2:68][CH2:67][C@H:52]1[C:53]([NH:55][C@H:56]([C:64]([OH:66])=[O:65])[CH2:57][CH2:58][CH2:59][NH:60][C:61](=[NH:63])[NH2:62])=[O:54]>O1CCOCC1.O>[C:24]([O:28][C:29]([NH:31][C@H:32]([C:48]([N:51]1[CH2:69][CH2:68][CH2:67][C@H:52]1[C:53]([NH:55][C@H:56]([C:64]([OH:66])=[O:65])[CH2:57][CH2:58][CH2:59][NH:60][C:61](=[NH:62])[NH2:63])=[O:54])=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39])=[O:30])([CH3:25])([CH3:26])[CH3:27]

Participants

6

Reactant 3

HCID 6316531,2,3,4,5-Pentafluoro-6-pentafluorophenoxybenzeneHCID 2724765Boc-Lys(Z)-OHHCID 178512874HCID 178512874, compound

Product 1

HCID 178454177HCID 178454177, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 53 g (0.1 mol) of pentafluorophenyl ether of tert.butyloxycarbonyl-Nε -benzyloxycarbonyl-lysine in 300 ml of dioxane there is added, under vigorous stirring, a solution of 23 g (0.08 mol) of prolyl-arginine II in 100 ml of water. After two hours the solvent is evaporated and the residue is dissolved in 150 ml of dimethylformamide. The solution is stirred for 48 hours at room temperature (25° C.), dimethylformamide is distilled-off to 1/3 volume, whereafter the reaction mixture is poured into 1 liter of diethyl ether. A further treatment is effected as described in the case of compound I. After recrystallization of the product from a mixture of ethylacetate-ethanol-diethyl ether (3:1:30) there are obtained 47 g (75%) of tert.butyloxycarbonyl-Nε -benzyloxycarbonyl-lysyl-prolyl-arginine having the following properties: M.p. 90° C., [L]D20 -39° (c 1.0; 10% CH3COOH); Rf =0.51/A, "Eastman"/, 0.82/B, "Eastman"/; Ehis =0.34 (pH 2.4).

Workup

  1. customAfter two hours the solvent is evaporated
  2. dissolutionthe residue is dissolved in 150 ml of dimethylformamide
  3. additionis poured into 1 liter of diethyl ether
  4. customAfter recrystallization of the product
  5. additionfrom a mixture of ethylacetate-ethanol-diethyl ether (3:1:30) there

Sources & evidence

ORD record
ord-be8e5eb66e5742bdb5f8e1687cdae35a
Source dataset
uspto-grants-1984_02
Patent number
US04434095

Reaction notes

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