p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 90770649, compound

HRID 1840455Notes

Reaction equation

HRID 1840455 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C@@H:7]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])[C:8](=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].C([Sn](CCCC)(CCCC)[C:32]1[S:36][C:35]2=[C:37]([S:40][C:41]([F:44])([F:43])[F:42])[N:38]=[CH:39][N:34]2[CH:33]=1)CCC>>[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])=[C:8]([C:32]3[S:36][C:35]4=[C:37]([S:40][C:41]([F:44])([F:43])[F:42])[N:38]=[CH:39][N:34]4[CH:33]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

3

Reactant 2

HCID 13504349p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylateHCID 22632113HCID 22632113, compound

Product 1

HCID 90770649HCID 90770649, compoundYield 14.8%

Procedure

The procedure of Example 1a) was repeated, except that 743 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 1.06 g 2-(tri-n-butylstannyl)-7-trifluoromethylthioimidazo[5,1-b]thiazole were used as the starting compounds. Thus, 172 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-trifluoromethylthioimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate was prepared.

Sources & evidence

ORD record
ord-82ab3852817b47029d0cdc2b2c1f9253
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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