(S)-4-Nitrophenyl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoate → HCID 178465162, compound

HRID 1763726Notes

Reaction equation

HRID 1763726 reaction equation
[ClH:1].[CH2:2]([NH:4][C:5](=[O:22])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:21])[C@H:12]([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:20])[NH2:19])[NH2:13])[CH3:3].[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].[CH2:2]([NH:4][C:5](=[O:22])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:21])[C@H:12]([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:19])[NH2:20])[NH:13][C:33](=[O:32])[C@H:34]([CH2:46][CH:47]([CH3:48])[CH3:49])[NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[CH3:3]

Participants

4

Reactant 2

HCID 97647(S)-4-Nitrophenyl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoateHCID 178465181HCID 178465181, compound

Product 1

HCID 178465162HCID 178465162, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 18.6 g. of L-arginyl-L-proline N-ethylamide hydrochloride (Ex.1,1) 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 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); ultraviolet in methanol λmax 257 E11 3.5.

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
  6. customthe product obtained solid
  7. customby precipitating from methanol with ethyl acetate
  8. customThe solid is dried at 40° C.

Sources & evidence

ORD record
ord-a4168d0ab6d24a2aa9ddba78a0ec2ae2
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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