HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclohexanepropanoic acid → 3-Cylcohexylpropanoic acid [(S)-2-(3,5-difluorophenyl)-1-((3S,9S,13S,15R,19S,22S)-15,19-Dimethyl-2,8,12,18,21-pentaoxo-11-oxa-1,7,17,20-tetraaza-tetracyclo[20.4.0.03,7.013,17] hexacos-9-ylcarbamoyl)-ethyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclohexanepropanoic acid | HCID 69702 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | (S)-2-(3,5-Difluorophenyl)-1-((3S,9S,13S,15R,19S,22S)-15, 19-Dimethyl-2,8,12,18,21-pentaoxo-11-oxa-1,7,17,20-tetraaza-tetracyclo[20.4.0.03,7.013,17]hexacos-9-ylcarbamoyl)-ethylammonium 2,2,2-trifluoroacetate | HCID 86598033 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | 3-Cylcohexylpropanoic acid [(S)-2-(3,5-difluorophenyl)-1-((3S,9S,13S,15R,19S,22S)-15,19-Dimethyl-2,8,12,18,21-pentaoxo-11-oxa-1,7,17,20-tetraaza-tetracyclo[20.4.0.03,7.013,17] hexacos-9-ylcarbamoyl)-ethyl]-amide | HCID 11578672 | — |
Reaction Steps
100 mg (0.13 mmol) of the compound from example 29A and 22.0 mg (0.14 mmol) of 3-cyclohexylpropionic acid are introduced under argon into anhydrous dimethylformamide (1 ml) at 0° C. and then 54.0 mg (0.14 mmol) of HATU and 0.025 ml (0.14 mmol) of ethyldiisopropylamine are added. After 30 min, a further 0.05 ml (0.29 mmol) of ethyldiisopropylamine are added to the reaction mixture. The reaction mixture is stirred overnight with slow warming to RT. The reaction solution is subjected directly to an RP-HPLC using acetonitrile/water as eluent. In the course of this, 50 mg (49% of th.) of a colorless solid are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07405201B2 |
| Source dataset | uspto-grants-2008_07 |
| ORD ID | ord-f3abb474b9b64c2ea737105e04240847 |
| Source note | uspto-grants-2008_07 |