HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → 5(S)-(Boc-Amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-[(p-benzyloxylphenyl)methyl]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)-[(p-benzyloxyphenyl)methyl]-hexanoic acid | HCID 22874295 | — |
| 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)-[(p-benzyloxylphenyl)methyl]hexanoic acid | HCID 15659562 | — |
Reaction Steps
Analogously to Example 1j), 1.4 g (2.69 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-benzyloxyphenylmethyl)-hexanoic acid in 2.9 ml of DMF are silylated with 1.87 g (12.4 mmol) of tert-butyldimethylchlorosilane and 1.5 g (22 mmol) of imidazole. Hydrolysis of the silyl ester function with 2.2 g of potassium carbonate in 63 ml of methanol/THF/water 3:1:1 and column chromatography (SiO2, hexane/ethyl acetate 2:1) of the crude product yields the title compound: TLC Rf (D)=0.17; tRet (II)=33.7 min; FAB-MS (M+H)+ =634.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05643878 |
| Source dataset | uspto-grants-1997_07 |
| ORD ID | ord-e25577331ef64253bee22e544175c934 |
| Source note | uspto-grants-1997_07 |