HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyloxycarbonyl-asparagine → {(S)-1-[1-Benzyl-3-((S)-2-benzyloxycarbonylamino-3-carbamoyl-propanoylamino)-2-hydroxy-4-phenyl-butylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyloxycarbonyl-asparagine | HCID 75314 | — |
| Reactant | 4-Amino-2-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentane | HCID 14704377 | — |
| Reactant | 2-Amino-4-(Cbz-asparaginyl-amino)-1,5-diphenyl-3-hydroxypentane | HCID 22845587 | — |
| Solvent | Chloroform methanol | HCID 21584188 | — |
| Product | {(S)-1-[1-Benzyl-3-((S)-2-benzyloxycarbonylamino-3-carbamoyl-propanoylamino)-2-hydroxy-4-phenyl-butylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester | HCID 3011025 | 75% |
Reaction Steps
Using the procedure of Example 55 but replacing Cbz-Val-OH with Cbz-Asn-OH and replacing the resultant compound of Example 11 with the resultant compound of Example 67 gave, after silica gel chromatography using methanol/chloroform, the desired compound (RF 0.4; 2.5% methanol/2% isopropylamine/chloroform) in 75% yield, m.p. 234°-236° C. (dec). Mass spectrum (M+H)+ =767.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05545750 |
| Source dataset | uspto-grants-1996_08 |
| ORD ID | ord-0c8639d0d17546a990f3de3895904a03 |
| Source note | uspto-grants-1996_08 |