1,1'-Oxybis(4-nitrobenzene) → HCID 178512875, compound

HRID 1388865Notes

Reaction equation

HRID 1388865 reaction equation
[N+](C1C=CC(OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O.[CH2:20]([O:27][C:28]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([OH:34])=O)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH2:38][C@H:39]([C:47]([OH:49])=[O:48])[CH2:40][CH2:41][CH2:42][NH:43][C:44](=[NH:46])[NH2:45]>O1CCOCC1.O>[CH2:20]([O:27][C:28]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([NH:38][C@H:39]([C:47]([OH:49])=[O:48])[CH2:40][CH2:41][CH2:42][NH:43][C:44](=[NH:45])[NH2:46])=[O:34])=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 75681,1'-Oxybis(4-nitrobenzene)HCID 101987Benzyloxycarbonyl-L-prolineHCID 178418600HCID 178418600, compound

Product 1

HCID 178512875HCID 178512875, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 37 g (0.1 mol) of p-nitrophenyl ether of benzyloxycarbonylproline in 360 ml of dioxane there is added a solution of 16 g (0.09 mole) of arginine in 160 ml of water under vigorous stirring. After two hours the solvent is evaporated and the residue is dissolved in 100 ml of dimethylformamide. The solution is stirred at room temperature (25° C.) for 72 hours and then poured into 1 liter of ethylacetate. After residence of the reaction mixture for 12 hours in a cooler the resulting precipitate is filtered-off, washed on the filter with ethylacetate and diethyl ether. After recrystallization of the product from a mixture of ethanol-diethyl ether (1:5) there are obtained 35 g (96%) of benzyloxycarbonyl-prolyl-arginine having the following properties: melting point 137°-140° C., [L]D20 -46.6° (c 1.0; H2O); Rf 0.53 (A, "Eastman"); 0.66 (B, "Eastman"), Ehis 0.56 (pH 2.4).

Workup

  1. customAfter two hours the solvent is evaporated
  2. dissolutionthe residue is dissolved in 100 ml of dimethylformamide
  3. additionpoured into 1 liter of ethylacetate
  4. waitAfter residence of the reaction mixture for 12 hours in a cooler the resulting precipitate is filtered-off
  5. washwashed on the
  6. filtrationfilter with ethylacetate and diethyl ether
  7. customAfter recrystallization of the product
  8. additionfrom a mixture of ethanol-diethyl ether (1:5) there

Sources & evidence

ORD record
ord-008399b121dc40fab2eeea35016d717a
Source dataset
uspto-grants-1984_02
Patent number
US04434095

Reaction notes

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