3-Azidopropan-1-ol → HCID 178462291, compound

HRID 1072391Notes

Reaction equation

HRID 1072391 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:53](=[O:54])[N:6]2[C:7]([C:40]([O:42]CC3C=CC([N+]([O-])=O)=CC=3)=[O:41])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][CH:24]=[C:25]([C:27]([O:29]CC6C=CC([N+]([O-])=O)=CC=6)=[O:28])[CH:26]=5)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[N:55]([CH2:58][CH2:59][CH2:60]O)=[N+]=[N-]>>[NH2:55][CH2:58][CH2:59][CH2:60][N+:23]1[CH:24]=[C:25]([C:27]([OH:29])=[O:28])[CH:26]=[C:21]([C:19]([C:16]2[N:17]=[CH:18][N:13]3[CH:12]=[C:11]([C:8]4[C@H:9]([CH3:10])[C@@H:5]5[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:53](=[O:54])[N:6]5[C:7]=4[C:40]([O-:42])=[O:41])[S:15][C:14]=23)=[O:20])[CH:22]=1

Participants

3

Reactant 2

HCID 109969743-Azidopropan-1-olHCID 91431965HCID 91431965, compound

Product 1

HCID 178462291HCID 178462291, compoundYield 16.5%

Procedure

The title compound (11.5 mg) was prepared in the same manner as in steps a) and b) of Example 4, except that 97.2 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-[5-(4-nitrobenzyloxycarbonyl)pyridin-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate and 27.0 mg of 3-azido-1-propanol were used as the starting compounds.

Sources & evidence

ORD record
ord-afa959bbf48d41288d2dd5676afde9b6
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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