HuagongsheHuagongshe Chemistry Print Report · For research reference only
9-Fluorenylmethyl chloroformate → 9-Fluorenylmethyl carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 9-Fluorenylmethyl chloroformate | HCID 34367 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | tert-butyl (2S,3S)-2-[3-({2-[(isopropylamino)methyl]-1,3-thiazol-4-yl}methyl)-2-oxo-1-imidazolidinyl]-3-methylpentanoate | HCID 66889849 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 9-Fluorenylmethyl carbamate | HCID 736301 | 141.4% |
Reaction Steps
A solution of the product of Example 283A (59 mg) in acetonitrile (0.9 mL) and water (0.3 mL) was treated with NaHCO3 (34 mg, 2.4 equivalents) followed by 9-fluorenylmethyl chloroformate (53 mg, 1.2 equivalents) at 25° C. for 1.5 h. The solvents were evaporated and the residue was purified using ethyl acetate:chloroform (1:4) to give 47 mg (40%) of FMOC-amine which was dissolved in dichloromethane (0.5 mL) and trifluoroacetic acid (0.5 mL) and stirred at 25° C. for 1 h. The solvents were evaporated, and the acid was used directly for the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08193227B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-97d43fb05c84418194af49e088543030 |
| Source note | uspto-grants-2012_06 |