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

HRID 355525노트

반응식

HRID 355525 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b91027d7b9ec41fb8a8f315d0fdbc944
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830868

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