(2S,3R)-3-(tert-butoxy)-2-(((tert-butoxy)carbonyl)amino)butanoic acid → 4-{[(2S,4EZ)-2-(5-{(1S,2R)-2-tert-butoxy-1-[(tert-butoxycarbonyl) amino]propyl}-1,2,4-oxadiazol-3-yl)-4-(methoxyimino)pyrrolidinyl]carbonyl}-1,1'-biphenyl

HRID 1242600Notes

Reaction equation

HRID 1242600 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[C:17](=[N:19][OH:20])[NH2:18])=[O:8])=[CH:3][CH:2]=1.[C:27]([O:31][C@H:32]([CH3:45])[C@H:33]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:34](O)=O)([CH3:30])([CH3:29])[CH3:28]>>[C:27]([O:31][C@H:32]([CH3:45])[C@@H:33]([C:34]1[O:20][N:19]=[C:17]([C@@H:10]2[CH2:11][C:12](=[N:14][O:15][CH3:16])[CH2:13][N:9]2[C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:6][CH:5]=2)=[O:8])[N:18]=1)[NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])([CH3:30])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 7015770(2S,3R)-3-(tert-butoxy)-2-(((tert-butoxy)carbonyl)amino)butanoic acidHCID 90995821(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N'-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide2×

Product 1

HCID 587145874-{[(2S,4EZ)-2-(5-{(1S,2R)-2-tert-butoxy-1-[(tert-butoxycarbonyl) amino]propyl}-1,2,4-oxadiazol-3-yl)-4-(methoxyimino)pyrrolidinyl]carbonyl}-1,1'-biphenylYield 48%

Procedure

Following the general method as outlined in Example 15, starting from (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N′-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide (Intermediate 8) and (2S,3R)-3-tert-butoxy-2-[(tert-butoxycarbonyl)amino]butanoic acid, the title compound, 4-{[(2S,4EZ)-2-(5-{(1S,2R)-2-tert-butoxy-1-[(tert-butoxycarbonyl)amino]propyl}-1,2,4-oxadiazol-3-yl)-4-(methoxyimino)pyrrolidinyl]carbonyl}-1,1′-biphenyl, was obtained in 48% yield (85.9% purity by HPLC).

Sources & evidence

ORD record
ord-5f2a3a407b0d4e28991971e494050130
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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