HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2,5-Dioxo-1-pyrrolidinyl (αR)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-naphthalenepropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | (2R)-2-(((tert-butoxy)carbonyl)amino)-3-(naphthalen-2-yl)propanoic acid | HCID 2734481 | — |
| Product | 2,5-Dioxo-1-pyrrolidinyl (αR)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-naphthalenepropanoate | HCID 131729706 | 90% |
Reaction Steps
Boc-D-2Nal-OH (315.4 g; 1.0 eq.) is dissolved in 2-propanol (6.8 L) at −10° C. and IBC (157 g; 1.15 eq.) and NMM (116 g; 1.15 eq.) is added. After stirring for 5-10 min a mixture of HONSu (230.1 g; 2.0 eq.) in 2-propanol (1.4 L) is added. Additional NMM (10.1 g; 0.1 eq.) is added. After half an hour water (0.82 L) is added to dissolve precipitated NMM.HCl. The product is isolated by filtration, washed with 2-propanol (1 L), and dried. Yield: 90%. HPLC purity: 98.3%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173770B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-d098f8665e1b4029a4f0883942f28366 |
| Source note | uspto-grants-2012_05 |