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

HRID 537627Notes

Reaction equation

HRID 537627 reaction equation
[NH2:1][C@@H:2]([C:15]([NH:17][C@H:18]([C:23]([NH:25][C@H:26]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH:41]([C:58]([O:60][CH2:61][CH:62]1[C:74]2[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:68]2[C:63]1=[CH:64][CH:65]=[CH:66][CH:67]=2)=[O:59])[C@@H:42]([C:55](O)=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49].CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl.C1C=CC2N(O)N=NC=2C=1>[NH:41]([C:58]([O:60][CH2:61][CH:62]1[C:74]2[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:68]2[C:63]1=[CH:64][CH:65]=[CH:66][CH:67]=2)=[O:59])[C@@H:42]([C:55]([NH:1][C@@H:2]([C:15]([NH:17][C@H:18]([C:23]([NH:25][C@H:26]([C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])[CH2:19][CH:20]([CH3:21])[CH3:22])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 13585941(2R)-6-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid2×HCID 131731957D-Lys(Boc)-Leu-Leu-OBzl

Product 1

HCID 131731956Fmoc-D-Lys(Boc)-D-Lys(Boc)-Leu-Leu-OBzlYield 85%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 6212ChloroformSolvent2×

Procedure

The obtained wet crystals of D-Lys(Boc)-Leu-Leu-OBzl (2-MeO-4-OC12OC22) were dissolved in chloroform (15 mL), Fmoc-D-Lys(Boc)-OH (444 mg, 948 μmol) and HOBt (12.8 mg, 94.7 μmol) were added at room temperature, and EDC HCl (200 mg, 1.04 mmol) was further added under ice-cooling. The mixture was warmed to room temperature and stirred overnight. Chloroform (20 mL), Fmoc-D-Lys(Boc)-OH (89 mg, 190 μmol) and EDC.HCl (40 mg, 210 μmol) were added, and the mixture was further stirred for 1 hr and concentrated under reduced pressure. The residue was precipitated with methanol (15 mL) to give Fmoc-D-Lys(Boc)-D-Lys(Boc)-Leu-Leu-OBzl (2-MeO-4-OC12OC22) (1.35 g, 85% yield relative to Bzl (2-MeO-4-OC12OC22)OH).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 1 hr
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was precipitated with methanol (15 mL)

Sources & evidence

ORD record
ord-1769a37cff0046a0bf2daf328e8f6032
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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