Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylthreonine | HCID 6364643 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | Fmoc-Thr(tBu)-NHBn | HCID 89583102 | 98% |
Reaction Steps
Benzylamine (0.270 g, 2.52 mmol) was coupled to Fmoc-Thr(tBu)-OH (S29, 1.00 g, 2.52 mmol) using the standard HATU coupling procedure. The reaction was diluted with Et2O (150 mL), and washed with 10% citric acid solution (60 mL), water (3×60 mL), and brine (60 mL). The organic layer was dried (MgSO4), filtered, and concentrated by rotary evaporation. The crude product was purified using flash chromatography (15% EtOAc/hexanes) to afford S30 as a white solid (1.20 g, 98% yield). Rf 0.53 (1:1 EtOAc/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=7.5 Hz, 2H), 7.61 (d, J=7.4 Hz, 2H), 7.44-7.27 (m, 9H), 6.06 (d, J=4.6 Hz, 2H), 4.50 (dd, J=7.8, 5.7 Hz, 2H), 4.44-4.37 (m, 2H), 4.27-4.14 (m, 3H), 1.24 (s, 9H), 1.04 (d, J=6.5 Hz, 3H); HRMS m/z calcd for C30H34N2NaO4 [MNa+] 509.2416, found 509.2226.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09145440B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-b48a2226feeb40cd80acfe1c7e44b6e2 |
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| Source note | uspto-grants-2015_09 |
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