Dicyclohexylcarbodiimide → Z-Trp-Pro-OBut

HRID 1154157

反応式

HRID 1154157 の反応式
C1CCC(N=C=NC2CCCCC2)CC1.[NH:16]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:17]([C:28]([OH:30])=O)[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:41]1[CH2:52][CH2:51][CH2:50][C@H:42]1[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:16]([C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[C@H:17]([C:28]([N:41]1[CH2:52][CH2:51][CH2:50][C@H:42]1[C:43]([O:45][C:46]([CH3:48])([CH3:49])[CH3:47])=[O:44])=[O:30])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 101176benzyloxycarbonyl-L-tryptophanHCID 6453108L-Proline 1,1-dimethylethyl ester

生成物 1

HCID 13178803Z-Trp-Pro-OBut

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

10.92 g (53 mmoles) of DCC are added at 0° C. to a solution of 16.9 g (50 mmoles) of Z-Trp-OH, 8.55 g (50 mmoles) of H-Pro-OBut and 6.75 g (50 mmoles) of HOBt in 75 ml of dimethylformamide. The mixture is stirred for 2 hours at 0° C. and left to stand overnight at room temperature. The precipitate is filtered off and the filtrate is concentrated. The residue is worked up analogously to Example 1 a. The residue is triturated with ether. Yield 19.49 g (79%), melting point 173°, [α]D25 =-54.2° (c=1, dimethylformamide).

後処理

  1. waitleft
  2. waitto stand overnight at room temperature
  3. filtrationThe precipitate is filtered off
  4. concentrationthe filtrate is concentrated
  5. customThe residue is triturated with ether
  6. customYield 19.49 g (79%), melting point 173°, [α]D25 =-54.2° (c=1, dimethylformamide)

出典と根拠

ORDレコード
ord-d31d4dc102284d9abf1553600d7eff4d
出典データセット
uspto-grants-1984_12
特許番号
US04487764

関連ノート

読み込み中…