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Ethylmorpholine → Z-D-Trp-D-Phe-OMe

HRID 596349
ノート
印刷プレビュー

反応式

HRID 596349 の反応式
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:26][O:27][C:28]([C@H:30]([NH2:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].Cl.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CO.C(Cl)(Cl)Cl>[CH3:26][O:27][C:28](=[O:29])[C@@H:30]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:38][C:13](=[O:14])[C@@H:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[NH:1][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 700663N-(Benzyloxycarbonyl)-D-tryptophanHCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

生成物 1

HCID 68125752Z-D-Trp-D-Phe-OMe

試薬・触媒・溶媒

3
HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of Z-D-Trp-OH (3.62 g, 10.7 mmoles), H-D-Phe-Ome.HCl (2.3 g, 10.7 mmoles) and 1-hydroxybenzotriazole (2.89 g, 21.4 mmoles) in dry DMF (25 ml) is cooled to 0° C and N-ethylmorpholine (1.37 ml, 10.7 mmoles) is added. A cold (0° C) solution of DCC (2.27 g, 11 mmoles) in DMF (6 ml) is added dropwise and the reaction mixture is stirred for 1 hr at 0° C and 1 hr at room temperature. The reaction mixture is then cooled to 0° C, filtered, the filtrate evaporated under reduced pressure and taken upon in EtOAc. The EtOAc solution is washed with saturated NaHCO3 solution, water, cold citric acid (2N), water, saturated NaHCO3 solution and saturated NaCl solution, dried with MgSO4, and evaporated under reduced pressure to afford the crude title product which is subjected to chromatography on a column of silica gel (500 g) with CHCl3 containing MeOH (1%) as eluent. The eluates are evaporated under reduced pressure and the residue is crystallized from EtOAc-petroleum ether to give the title compound; mp 130° - 131° C, [α]D25 = +34.1° (c = 1, DMF).

後処理

  1. temperatureThe reaction mixture is then cooled to 0° C
  2. filtrationfiltered
  3. customthe filtrate evaporated under reduced pressure
  4. washThe EtOAc solution is washed with saturated NaHCO3 solution, water, cold citric acid (2N), water, saturated NaHCO3 solution and saturated NaCl solution
  5. dry with materialdried with MgSO4
  6. customevaporated under reduced pressure
  7. customto afford the crude title product which
  8. customThe eluates are evaporated under reduced pressure
  9. customthe residue is crystallized from EtOAc-petroleum ether

出典と根拠

ORDレコード
ord-6f7a7986ca6b41c9b6d3648bf620668a
出典データセット
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04010260

反応ノート

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