Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | Boc-D-phenylalanine | HCID 637610 | — |
| Reactant | HCID 22313260 | HCID 22313260 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66688142 | HCID 66688142 | 85% |
Reaction Steps
6.7 g of carbonyldiimidazole is added to a solution of 10 g of Boc-D-Phe-OH in 80 ml of dichloromethane, cooled to 0° C. The resulting solution is maintained under stirring at 0° C. for 1 hour. A solution consisting of 8.0 g of (11) in 20 ml of dichloromethane is then dripped into the reaction mixture at a rate such that the temperature does not exceed 5° C. The solution is maintained under stirring at 0° C. for 1 hour, and at ambient temperature for 2 hours. 100 ml of 1M NaOH is added to the mixture, the two phases are separated, the organic phase is washed with water (2×), and after a low-pressure solvent change with ethyl acetate, compound (12) is crystallised from ethyl acetate to obtain 14.64 g of white solid. Yield 85%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08431684B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-bcc31fdfc5ab417cb9d61a0c699b6734 |
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| Source note | uspto-grants-2013_04 |
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