Dicyclohexylcarbodiimide → Nalpha-Benzyloxycarbonyl-O-benzyl-L-tyrosyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucine methyl ester

HRID 2083831Notes

Reaction equation

HRID 2083831 reaction equation
[CH3:1][O:2][C:3](=[O:50])[C@H:4]([CH2:46][CH:47]([CH3:49])[CH3:48])[NH:5][C:6](=[O:45])[C@@H:7]([CH2:41][CH:42]([CH3:44])[CH3:43])[NH:8][C:9](=[O:40])[C@H:10]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH:11][C:12](=[O:31])[C@H:13]([CH2:29][OH:30])[NH:14][C:15](=[O:28])[C@H:16]([CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[NH2:17].[CH2:51]([O:58][C:59]([NH:61][C@H:62]([C:78](O)=[O:79])[CH2:63][C:64]1[CH:69]=[CH:68][C:67]([O:70][CH2:71][C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)=[CH:66][CH:65]=1)=[O:60])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:50])[C@H:4]([CH2:46][CH:47]([CH3:49])[CH3:48])[NH:5][C:6](=[O:45])[C@@H:7]([CH2:41][CH:42]([CH3:43])[CH3:44])[NH:8][C:9](=[O:40])[C@H:10]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=1)[NH:11][C:12](=[O:31])[C@H:13]([CH2:29][OH:30])[NH:14][C:15](=[O:28])[C@H:16]([CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[NH:17][C:78](=[O:79])[C@H:62]([CH2:63][C:64]1[CH:65]=[CH:66][C:67]([O:70][CH2:71][C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=2)=[CH:68][CH:69]=1)[NH:61][C:59]([O:58][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:60]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 47600Z-Tyr(Bzl)-OHHCID 757711-HydroxybenzotriazoleHCID 54330961L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucine methyl ester

Product 1

HCID 86735668Nalpha-Benzyloxycarbonyl-O-benzyl-L-tyrosyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucine methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The above product, 2.0 g. of L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucine methyl ester, is dissolved in 70 ml. of dimethylformamide and cooled in an ice bath. Nα -Benzyloxycarbonyl-O-benzyl-L-tyrosine, 970 mg., 355 mg. of 1-hydroxybenztriazole and 545 mg. of dicyclohexylcarbodiimide are added. The reaction is stirred at ice bath temperature for several hours, then to room temperature and finally at room temperature for twenty-four hours. The mixture is filtered and the filtrate evaporated under reduced pressure. The residue is dissolved in 400 ml. of ethyl acetate, 20 ml. of water and 20 ml. of 0.5N hydrochloric acid. The ethyl acetate is separated, washed with saturated salt solution, with 0.5N sodium bicarbonate solution, again with saturated salt solution and is evaporated to a solid residue; 2.81 g.

Workup

  1. waitto room temperature and finally at room temperature for twenty-four hours
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in 400 ml
  5. customThe ethyl acetate is separated
  6. washwashed with saturated salt solution, with 0.5N sodium bicarbonate solution, again with saturated salt solution
  7. customis evaporated to a solid residue

Sources & evidence

ORD record
ord-e9ca9356bcc449cabfcf05f464dbba6a
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

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