1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Fmoc-D-Lys(Boc)-Leu-Leu-OBzl

HRID 537626Notes

Reaction equation

HRID 537626 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:25]([C:42]([O:44][CH2:45][CH:46]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:52]2[C:47]1=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:43])[C@@H:26]([C:39](O)=[O:40])[CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl.C1C=CC2N(O)N=NC=2C=1>[NH:25]([C:42]([O:44][CH2:45][CH:46]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:52]2[C:47]1=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:43])[C@@H:26]([C:39]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6])=[O:40])[CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13585941(2R)-6-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acidHCID 54422096Leu-Leu-OBzl

Product 1

HCID 131731955Fmoc-D-Lys(Boc)-Leu-Leu-OBzlYield 86%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 6212ChloroformSolvent

Procedure

The obtained wet crystals of Leu-Leu-OBzl (2-MeO-4-OC12OC22) were dissolved in chloroform (13 mL), Fmoc-D-Lys(Boc)-OH (481 mg, 1.03 mmol) and HOBt (13.9 mg, 103 μmol) were added at room temperature, and EDC HCl (216 mg, 1.13 mmol) was further added under ice-cooling. The mixture was warmed to room temperature, stirred overnight and concentrated under reduced pressure. The residue was precipitated with methanol (10 mL) to give Fmoc-D-Lys(Boc)-Leu-Leu-OBzl (2-MeO-4-OC12OC22) (1.14 g, 86% yield relative to Bzl (2-MeO-4-OC12OC22)OH).

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was precipitated with methanol (10 mL)

Sources & evidence

ORD record
ord-8be5fd0165ee4092b1346e02c8280c07
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

Loading…