HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butanol → 4-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Diisopropylcarbodiimide | HCID 12734 | — |
| Reactant | 4-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acid | HCID 285247 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester | HCID 53888193 | 54.2% |
Reaction Steps
To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid (8.0 g, 28.78 mmol) in DCM (35 mL) and DMF (35 mL) is added t-butanol (10 mL, 105.4 mmol) and DMAP (1.4 g, 11.50 mmol). DIPC (10 mL) is added portionwise over 1 h. The resulting mixtures stirs 18 h. The mixture is mounted onto SiO2 and purified by flash chromatography (gradient elution: 0-60% EtOAc/Hep) which affords 5.2 g of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.14 (m, 2H) 1.30 (m, 2H) 1.38 (m, 9H) 1.82 (m, 4H) 2.07 (m, 1H) 3.20 (m, 1H) 3.47 (m, 3H) 4.99 (m, 2H) 7.27 (m, 5H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08691756B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-5b99d01e798e4d879c9c0680f8f078bb |
| Source note | uspto-grants-2014_04 |