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

HRID 2083831ノート

反応式

HRID 2083831 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e9ca9356bcc449cabfcf05f464dbba6a
出典データセット
uspto-grants-1978_04
特許番号
US04086219

反応ノート

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