HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → 4-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | N-Benzyloxycarbonyl-beta-alanine | HCID 75313 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | H-Asp(O-tBu)-Phe-O-tBu | HCID 12968763 | — |
| Product | 4-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartate | HCID 111082 | — |
| Product | tert-butyl (2S)-2-amino-3-phenylpropanoate | HCID 6931633 | — |
Reaction Steps
834 mg of HBTU and 0.24 ml of N-methylmorpholine were added at 0° C. under argon to a solution of 446 mg of Z-β-Al-a-OH and 785 mg of H-Asp(O-tBu)-Phe-O-tBu (obtained from the condensation of Z-Asp(O-tBu)-OH with H-Phe-O-tBu followed by hydrogenolysis). After 5 hours, the mixture was concentrated and the residue was partitioned in ethyl acetate/5% NaHCO3. The organic phase was washed with water and 1M KHSO4. The organic extracts were dried, filtered and concentrated. The residue was recrystallised from ethyl acetate/diisopropyl ether resulting in 592 mg of Z-β-Ala-Asp(O-tBu)-Phe-O-tBu, m.p. 138°-139° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05273982 |
| Source dataset | uspto-grants-1993_12 |
| ORD ID | ord-83753e6947ab4843bcc0f19dd8d8f05d |
| Source note | uspto-grants-1993_12 |