HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → Fmoc-Cys(Trt)-OMe
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine | HCID 128239 | — |
| Reactant | (R)-methyl 2-amino-3-(tritylthio)propanoate | HCID 10429690 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Fmoc-Cys(Trt)-OMe | HCID 59278482 | — |
Reaction Steps
and H2N-Cys(Trt)-OMe 26. 7.2 g (12.3 mmol) of Fmoc-Cys(Trt)-OH was dissolved in 70 ml of MeOH and added 1.5 ml of conc. sulfuric acid. The reaction mixture was refluxed for 4 hr, the solvent was removed. The mixture was then mixed with ethyl acetate, and washed with water, saturated NaHCO3, and brine. Removing the solvent under vacuum gave 25 as a white foamy solid. The crude product was dissolved in 20 ml of 20% piperidine solution in DMF. After 2 hr, the solvent was removed. Silica gel chromatography (CH2Cl2: MeOH=10:1) gave 4.0 g (86% two step yield) of 26 as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07888055B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-e55b6ce1bc0f4993adb3aac24f127b1e |
| Source note | uspto-grants-2011_02 |