HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | (1R,2R,4R)-2-tert-butyl 1-methyl 4-(tert-butyldiphenylsilyloxy)cyclohexane-1,2-dicarboxylate | HCID 58282737 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | (1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid | HCID 58282618 | 63% |
Reaction Steps
A solution of compound 37 (4.2 mmol) and LiOH (16.8 mmol) in THF/H2O 1/1 (40 mL) was stirred at room temperature for 16 hrs. The reaction mixture was neutralized with 1N HCl to pH 2, and then extracted with DCM (100 mL). Organics were concentrated under reduced pressure and purified by chromatography on silica gel (Cyclohexane/EtOAc) to yield compound 38 as pale yellow oil in 63% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09284307B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-d7a89dc963344017b905e12ac92b2e2e |
| Source note | uspto-grants-2016_03 |