HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → Z-Phe-Ser(OCH2C6H5)-Ala-OCH3
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Benzyloxycarbonyl-L-phenylalanine | HCID 70878 | — |
| Reactant | L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- | HCID 90234 | — |
| Reactant | Alanine methyl ester hydrochloride | HCID 2733257 | — |
| Reactant | Boc-Ser(OCH2C6H5)-Ala-OCH3 | HCID 54537467 | — |
| Reactant | H-Ser(OCH2C6H5)-Ala-OCH3 trifluoroacetate | HCID 131715028 | — |
| Product | Z-Phe-Ser(OCH2C6H5)-Ala-OCH3 | HCID 131715027 | 74% |
Reaction Steps
First, Boc-Ser(OCH2C6H5)-OH (4.93 g, 16.7 mmol) was coupled to H-Ala-OCH3.HCl (2.80 g, 20.0 mmol) by a mixed anhydride procedure to yield an oil, 6.1 g. Boc-Ser(OCH2C6H5)-Ala-OCH3 was then deblocked with trifluoroacetic acid, and the resulting product, H-Ser(OCH2C6H5)-Ala-OCH3.trifluoroacetate (6.15 g, 15.6 mmol), was coupled to Z-Phe-OH (3.89 g, 13.0 mmol) using a mixed anhydride procedure. This product was crystallized from ethyl acetate to yield 5.4 g of Z-Phe-Ser(OCH2C6H5)-Ala-OCH3 (m.p. 158°-159°).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04636492 |
| Source dataset | uspto-grants-1987_01 |
| ORD ID | ord-cd7de0a3e12a439e99e229f63dba88b7 |
| Source note | uspto-grants-1987_01 |