HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyldiphenylchlorosilane | HCID 94078 | — |
| Reactant | (S)-Benzyl 2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate | HCID 11056397 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid benzyl ester | HCID 66854935 | — |
Reaction Steps
To a solution of 2.5 g (S)-2-tert-Butoxycarbonylamino-5-hydroxy-pentanoic acid benzyl ester (prepared by adapting the procedure described by Diederichsen et al., Org. Biomol. Chem., 2005, 3, 1058) in 50 ml DMF were added 2.0 ml TBDPSCl, 1.2 ml triethylamine and 95 mg DMAP and the resulting suspension was stirred for 4 days. The solvent was evaporated, the residue dissolved in ethyl acetate and washed with aqueous LiCl (4 w/w), 0.1 M HCl and saturated NaHCO3. The crude product obtained after evaporation of the solvent was purified by chromatography on silica using heptane/ethyl acetate 12/1 as eluent. Yield: 2.0 g colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08426420B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-0c9d88b28b5440678ebc7878f3d04a87 |
| Source note | uspto-grants-2013_04 |