HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 73196385, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | HCID 11401906 | HCID 11401906 | — |
| Reactant | (S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide | HCID 15517727 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 73196385 | HCID 73196385 | 14% |
Reaction Steps
O-Benzyl-L-tyrosine-t-butyl-amide (Ia, 0.5 g, 1.53 mmol) was dissolved in DMF (8 mL) and treated with diisopropylethylamine (0.8 mL, 4.6 mmol), N-cyclohexyl-N-methyl-leucine (Iid, 0.34 g, 1.53 mmol), and HBTU (0.58 g, 1.53 mmol). The reaction was stirred for 2 hours, then diluted with EtOAc (100 mL), washed with saturated bicarbonate solution (2×100 mL), brine (100 mL), dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 50% EtOAC/hexane. The resulting material was chromatographed again on silica gel eluting with 8% acetone/CH2Cl2 to give 0.11 g (14%) of the title compound. MS: 537 (M+1 for C33H49N3O3); TLC: SiO2, Rf 0.57 (10% MeOH/CH2Cl2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06117841 |
| Source dataset | uspto-grants-2000_09 |
| ORD ID | ord-8d0d7bb5911844e093ff55da787c039f |
| Source note | uspto-grants-2000_09 |