Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1-Iodo-3-methylbutane | HCID 10924 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 58017458 | HCID 58017458 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58017467 | HCID 58017467 | 65% |
Reaction Steps
To a solution of N-(3 Methoxyphenylsulfonyl)D-tert-leucine benzyl ester (1.31 g, 3.35 mmol) in DMF (10 ml) is added K2CO3 (1.87 g, 13.4 mmol) followed by 1-iodo-3-methyl butane (1.33 g, 6.69 mmol) and the reaction mixture is heated to 70° C. overnight. The reaction is cooled to room temperature and then poured over 1 N HCl and extracted with Ethyl Acetate. The organics are washed with brine, dried over MgSO4 and concentrated. The crude product is purified by column chromatography eluting with a gradient of 5-40% (Hex-EtOAc) affording the title compound as a colorless oil (1.0 g, 65% yield). Mass spectrum (462.3; M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08314148B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-6abd9df5b8964b86a4fda629429fe7f6 |
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| Source note | uspto-grants-2012_11 |
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