O-Benzylhydroxylamine → 2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide

HRID 651806Notes

Reaction equation

HRID 651806 reaction equation
C(O[C:6]([C@H:8]([C@@H:18]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:19]([NH:21][NH:22][C:23](=[O:26])[CH2:24][NH2:25])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])(C)(C)C.[CH2:31]([O:38][NH2:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[O:40]1CCCC[CH:41]1ON>>[CH2:31]([O:38][NH:39][C:6]([C@H:8]([C@@H:18]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:19]([NH:21][N:22]1[C:23](=[O:26])[CH2:24][NH:25][C:41]1=[O:40])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:7])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 102313O-BenzylhydroxylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 867573112(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2'-glycinyl-4-methylvalerohydrazide

Product 1

HCID 867573102(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide

Procedure

In a manner analagous to that described in Example 1, parts (vi)-(viii), but using 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2′-glycinyl-4-methylvalerohydrazide and O-benzylhydroxylamine in place of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-glycinyl-4-methylvalerohydrazide and O-(tetrahydro-2H-pyran-2(RS)-yl)hydroxylamine respectively there was obtained 2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide in the form of a white solid.

Sources & evidence

ORD record
ord-a8b7aeb90523406281dba7c2cdcb3192
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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