(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*))-

HRID 52726Notes

Reaction equation

HRID 52726 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][CH2:10][O:11][C:12]([NH:14][C@H:15]([C:19]([OH:21])=O)[CH:16]([CH3:18])[CH3:17])=[O:13])[N:8]=1)([CH3:3])[CH3:2].[NH2:22][C@H:23]([C@@H:31]([OH:51])[CH2:32][C@@H:33]([NH:41][C:42]([O:44][CH2:45][C:46]1[S:50][CH:49]=[N:48][CH:47]=1)=[O:43])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][CH2:10][O:11][C:12]([NH:14][C@H:15]([C:19]([NH:22][C@H:23]([C@@H:31]([OH:51])[CH2:32][C@@H:33]([NH:41][C:42]([O:44][CH2:45][C:46]2[S:50][CH:49]=[N:48][CH:47]=2)=[O:43])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[CH:16]([CH3:17])[CH3:18])=[O:13])[N:8]=1)([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 10812314(2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexaneHCID 10829088N-((2-(2-isopropyl-4-thiazolyl)ethoxy)carbonyl)valine

Product 1

HCID 48295112-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*))-

Procedure

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.

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-ddd1837045f947009961dba2289bfff5
Source dataset
uspto-grants-1997_04
Patent number
US05616720

Reaction notes

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