Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Tert-butoxycarbonylalanine | HCID 85082 | — |
| Reactant | Benzyl octahydro-1H-indole-2-carboxylate hydrochloride | HCID 19902522 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67806908 | HCID 67806908 | — |
Reaction Steps
19 g of Boc-Ala-OH are dissolved in 100 ml of dimethylformamide, and 13 ml of N-ethylmorpholine, 13.5 g of HOBt and 29.6 g of octahydroindole-2-carboxylic acid benzyl ester hydrochloride are added to the solution. The mixture is cooled in an ice bath, 21 g of dicyclohexylcarbodiimide are added to it, and it is stirred for 15 hours at room temperature. The precipitated urea is filtered off under suction, and the filtrate is concentrated in vacuo and taken up in ethyl acetate. The solution is extracted 3 times in each case with aqueous KHSO4 solution, KHCO3 solution and saturated NaCl solution and the organic phase is concentrated in vacuo. Yield: 38.5 g. NMR: 1.26 (d, 3H); 1.40 (s, 9H); 1,1-2,4 (m, 12H); 3.2-3.9 (m, 2H); 5.28 (s, 2H); 7.31 (s, 5H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05401766 |
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| Source dataset | uspto-grants-1995_03 |
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| ORD ID | ord-66c018cfc7264a1d9ae9b5b3a5408218 |
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| Source note | uspto-grants-1995_03 |
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