Triethylamine → Cbz-His(1-Me)-Tyr(OBn)-Ser(OBn)-CO2Me

HRID 355525ノート

反応式

HRID 355525 の反応式
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[N:8]=[CH:7][N:6]([CH3:9])[CH:5]=1.[NH2:23][C@H:24]([C:40]([NH:42][C@H:43]([C:53]([C:55]([O:57][CH3:58])=[O:56])=[O:54])[CH2:44][O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:41])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:28][CH:27]=1.Cl.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl.C(Cl)(Cl)Cl>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:23][C@H:24]([C:40]([NH:42][C@H:43]([C:53]([C:55]([O:57][CH3:58])=[O:56])=[O:54])[CH2:44][O:45][CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)=[O:41])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:30][CH:31]=1)=[O:12])[CH2:3][C:4]1[N:8]=[CH:7][N:6]([CH3:9])[CH:5]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13490232(S)-2-(((Benzyloxy)carbonyl)amino)-3-(1-methyl-1H-imidazol-4-yl)propanoic acidHCID 131720926Tyr(OBn)-Ser(OBn)-CO2Me.HCl

生成物 1

HCID 131720925Cbz-His(1-Me)-Tyr(OBn)-Ser(OBn)-CO2Me

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

To a slurry of Cbz-His(1-Me) (from Step 1 above, 0.36 g, 1.2 mmol), Tyr(OBn)-Ser(OBn)-CO2Me.HCl (from Example 8, Step 1 above, 0.60 g, 1.2 mmol), DCC (0.30 g, 1.4 mmol), and HOBT (0.19 g, 1.4 mmol) in CH2Cl2 was added Et3N (0.17 mL, 1.2 mmol) and the mixture was stirred overnight at room temperature. The mixture was diluted with CHCl3, washed with saturated aqueous NaHCO3, brine, dried (MgSO4), and concentrated. Flash chromatography (1% MeOH:CHCl3) provided the title compound as a white solid, mp 161.5°-163.5° C.; FAB-MS 748 (m+1).

後処理

  1. washwashed with saturated aqueous NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-b91027d7b9ec41fb8a8f315d0fdbc944
出典データセット
uspto-grants-1998_11
特許番号
US05830868

反応ノート

読み込み中…