(S)-4-Nitrophenyl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoate → HCID 178465161, compound

HRID 866731Notes

Reaction equation

HRID 866731 reaction equation
[ClH:1].[NH2:2][C@H:3]([C:11]([N:13]1[CH2:22][CH2:21][CH2:20][C@H:14]1[C:15]([N-:17][CH2:18][CH3:19])=[O:16])=[O:12])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:10])[NH2:9].[N+](C1C=CC([O:32][C:33](=O)[C@H:34]([CH2:46][CH:47]([CH3:49])[CH3:48])[NH:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])=CC=1)([O-])=O>CN(C)C=O>[ClH:1].[CH2:39]([O:38][C:36]([NH:35][C@H:34]([C:33]([NH:2][C@H:3]([C:11]([N:13]1[CH2:22][CH2:21][CH2:20][C@H:14]1[C:15]([N-:17][CH2:18][CH3:19])=[O:16])=[O:12])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:9])[NH2:10])=[O:32])[CH2:46][CH:47]([CH3:48])[CH3:49])=[O:37])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 2

HCID 97647(S)-4-Nitrophenyl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoateHCID 178465180HCID 178465180, compound

Product 1

HCID 178465161HCID 178465161, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 18.6 g. of L-arginyl-L-prolyl-N-ethylamide hydrochloride and 7.2 g. of Nα -benzyloxycarbonyl-L-leucine p-nitrophenylester in 30 ml. of dimethylformamide is allowed to stand for four days, warmed to 50° C. for a half hour and evaporated at reduced pressure and 40° C. to yield an oil. A solid product is obtained by chromatography over silica gel, eluting with chloroform with increasing percent of methanol. Fraction selection is made on the basis of analytical thin layer chromatography and the product, Nα -benzyloxycarbonyl-L-leucyl-L-arginyl-L-prolyl-N-ethylamide hydrochloride, obtained solid by precipitating from methanol with ethyl acetate and then by dropping a methanol solution into ethyl ether. The solid is dried at 40° C. and reduced pressure; [α]D25 -68.4° (c 1, methanol).

Workup

  1. customevaporated at reduced pressure and 40° C.
  2. customto yield an oil
  3. customA solid product is obtained by chromatography over silica gel
  4. washeluting with chloroform
  5. temperaturewith increasing percent of methanol

Sources & evidence

ORD record
ord-663ce396021343ef917a3f578bf833f2
Source dataset
uspto-grants-1978_07
Patent number
US04101537

Reaction notes

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