HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Fmoc-D-Lys(Boc)-D-Lys(Boc)-Leu-Leu-OBzl
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | (2R)-6-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid | HCID 13585941 | — |
| Reactant | D-Lys(Boc)-Leu-Leu-OBzl | HCID 131731957 | — |
| Catalyst | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | Fmoc-D-Lys(Boc)-D-Lys(Boc)-Leu-Leu-OBzl | HCID 131731956 | 85% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08859732B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-1769a37cff0046a0bf2daf328e8f6032 |
| Source note | uspto-grants-2014_10 |