HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Boc-Pro-Val-NH2 | HCID 11141514 | — |
| Reactant | DCCI HOBt | HCID 21712060 | — |
| Product | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Product | Boc-L-valine amide | HCID 11241393 | — |
Reaction Steps
In such a synthesis, the lysine side chain is protected by a MSOC protective group introduced onto Boc-Lys-OH so as to form Boc-Lys(MSOC)-OH. The diprotected N(α),N(ε) lysine is coupled with Boc-Pro-Val-NH2, HCl by the conventional DCC/HOBt method. The Boc-Pro-Val-NH2, HCl reactant is in turn obtained in two steps from Boc-Pro-OH and Boc-Val-NH2. The overall yield is 33% calculated based on Boc-Lys(MSOC)-OH. The global synthesis scheme is illustrated in the scheme (I) hereunder:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07683026B2 |
| Source dataset | uspto-grants-2010_03 |
| ORD ID | ord-17fef5a278f94ff5bdd2b8d751b0c84a |
| Source note | uspto-grants-2010_03 |