HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (S)-Benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-4-phenylbutanamido)-4-methylpentanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzyl L-leucinate | HCID 6451313 | — |
| Reactant | (2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid | HCID 7018726 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-Benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-4-phenylbutanamido)-4-methylpentanoate | HCID 131735341 | 100% |
Reaction Steps
Referring to FIG. 45, DIPEA (2 mL, 12 mmol, 2.7 eq) was added to a mixture of Boc-HoPhe-OH (1.25 g, 4.4 mmol, 1 eq). H-Leu-OBn.TsOH (1.75 g, 4.5 mmol, 1.0 eq) and HATU (2 g, 5 mmol, 1.1 eq) in CH2Cl2 (50 mL) and the mixture was stirred for four hours at RT. The mixture was poured into 0.5N aq. HCl and extracted twice with CH2Cl2. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (SiO2, 0-30% EtOAc in heptanes) and product (2.7 g, 100%) was isolated as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309283B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-fbb72974d9864b1f91224abf0925e3fd |
| Source note | uspto-grants-2016_04 |