Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Reactant | HCID 69732763 | HCID 69732763 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 23586350 | HCID 23586350 | — |
Reaction Steps
The (2-hydroxy-2-phenylcarbamoyl-ethyl)-carbamic acid benzyl ester (250 mg, 1.045 mmol) was dissolved into 2 mL of dry DMF. To this was added PyBOP (652.3 mg, 1.254 mmol), HOBT (169.4 mg, 1.254 mmol), benzylamine (0.228 mL, 2.090 mmol) and DIPEA (0.728 mL, 4.18 mmol). The reaction stirred for 1.5 h. LC-MS analysis of the crude indicated complete consumption of the S.M. and the presence of the product. 40 mL of EtOAc was added and the organic mixture washed with 2×20 mL NH4Cl, 2×20 mL of H2O and 1×20 mL of brine. Dried organic phase with MgSO4, filtered and concentrated to a yellow film. Dissolved in CH2Cl2, applied to a SiO2 Column and purified (10-30% EtOAc/hexanes) to give a quantitative yield of (2-benzylcarbamoyl-2-hydroxy-ethyl)-carbamic acid benzyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06974870B2 |
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| Source dataset | uspto-grants-2005_12 |
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| ORD ID | ord-5df15e0571784c75b687e73d459cbced |
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| Source note | uspto-grants-2005_12 |
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