HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → 5(S)-(Boc-amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid | HCID 22874292 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | 5(S)-(Boc-amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid | HCID 22874316 | — |
Reaction Steps
Analogously to Example 1j), 2.7 g (6.25 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid in 30 ml of DMF are silylated with 4.33 g (28.8 mmol) of tert-butyldimethylchlorosilane and 3.51 g (51.3 mmol) of imidazole. Hydrolysis of the silyl ester function with 5.1 g of potassium carbonate in 100 ml of methanol/THF/water 4:1:1 yields the title compound after column chromatography (SiO2, hexane/ethyl acetate 2:1): tRet (I)=20.8 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05643878 |
| Source dataset | uspto-grants-1997_07 |
| ORD ID | ord-f9a60a54fd9f4e9ab4bf890e251032db |
| Source note | uspto-grants-1997_07 |