Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | 7-Bromo-2-(2-(tert-butyl(3-(3-(thiazol-5-yl)prop-2-ynyloxy)propyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid | HCID 58124792 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetic Anhydride | HCID 7918 | — |
| Product | HCID 58124867 | HCID 58124867 | 69.8% |
Reaction Steps
A mixture of 240 mg of 8d and 250 mg of sodium acetate in 5 ml of acetic anhydride was heated at 100° C. for 30 min. The reaction mixture was cooled, diluted with 10 ml of water and stirred for 1 hr at ambient temperature to hydrolyze excess anhydride. The mixture was then made alkaline with cold conc. aq. NH4OH and the product was extracted with ethyl acetate. The product thus isolated was purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate as eluent. The purified product isolated was treated with diethyl ether and gave 150 mg of crystalline material 8e. Rf (toluene/acetone 7/3) 0.50.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08431564B2 |
|---|
| Source dataset | uspto-grants-2013_04 |
|---|
| ORD ID | ord-5012570b1c5c42938c145af98be34598 |
|---|
| Source note | uspto-grants-2013_04 |
|---|
