HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formic Acid → HCID 58392673, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | 3,3-Dimethylbutanal | HCID 76335 | — |
| Reactant | Acetic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4-aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester hydrochloride | HCID 67353702 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 58392673 | HCID 58392673 | 73.1% |
Reaction Steps
A solution of compound 20 (900 mg, 1.800 mmol), 3,3-dimethylbutyraldehyde (904 μl, 7.20 mmol), formic acid (552 μl, 14.40 mmol) and TEA (251 μl, 1.800 mmol) in acetonitrile (45 ml) is irradiated with microwaves (140° C., 15 minutes). The reaction is partitioned between AcOEt and NaHCO3 solution. The organic layers are then washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated to give a oil which is purified by silica gel chromatography (from DCM:MeOH 100:0 to 98.5:1.5) to give the title compound (721 mg, 1.316 mmol, 73.1% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08481517B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-d9b4b1f101b0416aa68b772880494043 |
| Source note | uspto-grants-2013_07 |