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

HRID 355525Notes

Reaction equation

HRID 355525 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-b91027d7b9ec41fb8a8f315d0fdbc944
Source dataset
uspto-grants-1998_11
Patent number
US05830868

Reaction notes

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