1-Hydroxybenzotriazole → Boc-Leu-DTrp-OMe

HRID 1757291Notes

Reaction equation

HRID 1757291 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].O.[NH2:18][C@@H:19]([C:30]([O:32][CH3:33])=[O:31])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1.Cl.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>ClCCl.O>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:18][C@@H:19]([C:30]([O:32][CH3:33])=[O:31])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11448200methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate hydrochlorideHCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 14504288Boc-Leu-DTrp-OMeYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of Boc-Leu-OH.H2O (0.997 g) and DTrp-OMe.HCl (1.021 g) in dichloromethane (10 ml) were added TEA (0.6 ml) and HOBT.H2O (0.615 g) under argon. EDCI.HCl (0.769 g) was added to the mixture at 0°-5° C. The resulting reaction mixture was stirred at room temperature for 16 h, washed successively with water, 10% aq. citric acid, sat. NaHCO3 and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was triturated with hexane to give the product (1.665 g). FAB-MS(m/e,(C23H33N3O5 +H)+):432

Workup

  1. customThe resulting reaction mixture
  2. washwashed successively with water, 10% aq. citric acid, sat. NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-24f4bf5317bb4701b9d1351e02b67389
Source dataset
uspto-grants-1995_08
Patent number
US05444152

Reaction notes

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