HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → LY311727
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Bromotrimethylsilane | HCID 76113 | — |
| Reactant | [3-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-propyl]-phosphonic acid dimethyl ester | HCID 10504075 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | LY311727 | HCID 155922 | 97.2% |
Reaction Steps
[3-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester (150 mg, 0.33 mmol) and 0.35 mL (2.6 mmol) of trimethylsilyl bromide in 2 mL of methylene chloride was stirred for 16 hours, 5 mL of MeOH added, stirred 1.0 hour and concentrated at reduced pressure. The residue was crystallized from EtOAc/MeCN/HOAc/water to give 138 mg (97% yield) of [3-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid, mp, 194°-196° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05684034 |
| Source dataset | uspto-grants-1997_11 |
| ORD ID | ord-168535dd95734312afe0af35d9f81921 |
| Source note | uspto-grants-1997_11 |