p-Toluenesulfonic acid → Boc-Leu-DTrp(COOMe)-DNle-OBzl

HRID 977517Notes

Reaction equation

HRID 977517 reaction equation
[NH:1]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:2]([C:7]([NH:9][C@@H:10]([C:25](O)=[O:26])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]([O:23][CH3:24])=[O:22])[CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:35][C@@H:36]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH2:37][CH2:38][CH2:39][CH3:40].CC1C=CC(S(O)(=O)=O)=CC=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>ClCCl.O>[NH:1]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C@H:2]([C:7]([NH:9][C@@H:10]([C:25]([NH:35][C@@H:36]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH2:37][CH2:38][CH2:39][CH3:40])=[O:26])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]([O:23][CH3:24])=[O:22])[CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

9

Reactant 6

HCID 6101p-Toluenesulfonic acidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10922067H-D-Nle-ObzlHCID 131719297Boc-Leu-DTrp(COOMe)-OH

Product 1

HCID 15298069Boc-Leu-DTrp(COOMe)-DNle-OBzl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of Boc-Leu-DTrp(COOMe)-OH (50 mg), H-DNle-OBzl.TsOH (46 mg), NMM (13 μl) and HOBT.H2O (16 mg) in dichloromethane (1 ml) was added EDCI.HCl (22 mg) under ice cooling. After being stirred at room temperature for 2 h, the mixture was diluted with dichloromethane, washed with water, 10% aq. citric acid, sat. aq. NaHCO3 and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol/acetic acid=100/10/1 for development to give Boc-Leu-DTrp(COOMe)-DNle-OBzl (67 mg).

Workup

  1. washwashed with water, 10% aq. citric acid, sat. aq. NaHCO3 and brine successively
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol/acetic acid=100/10/1 for development

Sources & evidence

ORD record
ord-e6745e73c52544aeb1b377b879b2acb8
Source dataset
uspto-grants-1997_03
Patent number
US05614498

Reaction notes

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