HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(((Benzyloxy)carbonyl)amino)-2,2-dimethylpropanoic acid → 3beta-[(2,2-Dimethyl)-3-(carbobenzyloxyamino)propionyloxy]-androstane-6,17-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(((Benzyloxy)carbonyl)amino)-2,2-dimethylpropanoic acid | HCID 14551010 | — |
| Reactant | 3beta-Hydroxy-5alpha-androstan-6,17-dione | HCID 69012642 | — |
| Product | 3beta-[(2,2-Dimethyl)-3-(carbobenzyloxyamino)propionyloxy]-androstane-6,17-dione | HCID 69133468 | 92.3% |
Reaction Steps
Following the procedure described in Prepn. 68 and starting from 3β-hydroxyandrostane-6,17-dione (Prepn. 68, 0.50 g) and 3-(benzyloxycarbonylamino)-2,2-dimethylpropanoic acid (0.41 g), after purification by flash chromatography (SiO2; EtOAc:n-hexane 6:4) to give 3β-[(2,2-dimethyl)-3-(carbobenzyloxyamino)propionyloxy]-androstane-6,17-dione (0.81 g, 90%) was obtained. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.34 (5H, m), 5.07 (2H, s), 7.01 (1H, m), 4.57 (1H, m), 2.50-1.10 (22H, m), 1.10 (6H, s), 0.78 (3H, s), 0.70 (3H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609644B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-4edb8c85d576443a843b679d4041b8b9 |
| Source note | uspto-grants-2013_12 |