Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | 6-(((Phenylmethoxy)carbonyl)amino)hexanoic acid | HCID 74758 | — |
| Reactant | HCID 22556092 | HCID 22556092 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22556071 | HCID 22556071 | 76% |
Reaction Steps
Dissolved N-Cbz-6-aminohexanoic acid (784 mg, 2.96 mmole) into 10 mL of N,N-dimethylformamide and cooled to 0° C. Added triethylamine (1.65 mL, 11.8 mmole), stirred for 10 minutes, then added isobutylchloroformate (385 uL, 2.68 mmole). Stirred for 45 minutes and then added the crude methyl 4-[({[4-(methoxycarbonyl)-3-(phenylmethoxy)phenyl]methyl}-amino)-methyl]-2-(phenylmethoxy)benzoate hydrochloride from the step above (830 mg, 1.48 mmole). Let warm to room temperature and stirred for 3 hours. Diluted the reaction mixture with 1 N HCl and extracted with ethyl acetate. Dried the ethyl acetate layers with brine and anhydrous magnesium sulfate. Filtered, removed solvents in vacuo, and chromatographed on silica gel. Collected 870 mg (76% yield) of product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06156884 |
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| Source dataset | uspto-grants-2000_12 |
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| ORD ID | ord-2c58b837e004498a9f533931e4285a2a |
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| Source note | uspto-grants-2000_12 |
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