HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (2S,4S)-1-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | N-(tert-Butoxycarbonyl)-L-cyclohexylglycine | HCID 7004938 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (2S,4S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester trifluoroacetate | HCID 90220138 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2S,4S)-1-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester | HCID 118677402 | 93% |
Reaction Steps
To a solution of (S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid (Aldrich) (435 mg, 1.69 mmol) in DMF at 0° C. was added DIPEA (1.18 mL, 6.76 mmol) and HATU (674 mg, 1.77 mmol). After 30 minutes (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester trifluoroacetate (0.94 g, 1.69 mmol) was added in one portion. The cooling bath was removed and the mixture stirred for 1 h, diluted with water, the resulting white precipitate collected, washed with water and air-dried to give (2S,4S)-1-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester (1.07 g, 93%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409888B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-9ed1126acb5e4c8d85454db2acfc0951 |
| Source note | uspto-grants-2016_08 |