HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexane → 12-Oxa-2,7,10-triazatetradecanoic acid, 5-hydroxy-9-(1-methylethyl)-14-(2-(1-methylethyl)-4-thiazolyl)-8,11-dioxo-3,6-bis(phenylmethyl)-, 5-thiazolylmethyl ester, (3S-(3R*,5R*,6R*,9R*))-
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexane | HCID 10812314 | — |
| Reactant | N-((2-(2-isopropyl-4-thiazolyl)ethoxy)carbonyl)valine | HCID 10829088 | — |
| Product | 12-Oxa-2,7,10-triazatetradecanoic acid, 5-hydroxy-9-(1-methylethyl)-14-(2-(1-methylethyl)-4-thiazolyl)-8,11-dioxo-3,6-bis(phenylmethyl)-, 5-thiazolylmethyl ester, (3S-(3R*,5R*,6R*,9R*))- | HCID 482951 | — |
Reaction Steps
Using the procedure of Example 1U, but replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine with N-((2-(2-isopropyl-4-thiazolyl)ethoxy)carbonyl)valine and replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane provided, after purification by silica gel chromatography using 99:1 CHCl3:CH3OH, 50 mg (30%) of the desired compound (Rf 0.3, 95:5 CHCl3:CH3OH) as a solid, mp 159-160° C. Mass spectrum: (M+H)+=722 HRMS. Exact mass calcd for C37H47N5O6S2: 722.3046. Found: 722.3036.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06667404B2 |
| Source dataset | uspto-grants-2003_12 |
| ORD ID | ord-aad851783d454109aab1f4345c55605c |
| Source note | uspto-grants-2003_12 |