5-(3-(Benzyloxy)-7-bromo-1-fluoronaphthalen-2-yl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide → 5-[8-Fluoro-6-hydroxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-2,2-dimethyl-pentanoic acid

HRID 889266Notes

Reaction equation

HRID 889266 reaction equation
C([O:8][C:9]1[C:10]([N:21]2[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]2)=[C:11]([F:20])[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)C1C=CC=CC=1.[CH3:29][C:30]([CH3:37])([CH2:34][CH:35]=[CH2:36])[C:31]([OH:33])=[O:32].B1C2CCCC1CCC2>[OH-].[OH-].[Pd+2].[Pd]>[F:20][C:11]1[C:10]([N:21]2[CH2:22][C:23](=[O:28])[NH:24][S:25]2(=[O:27])=[O:26])=[C:9]([OH:8])[CH:18]=[C:17]2[C:12]=1[CH:13]=[C:14]([CH2:36][CH2:35][CH2:34][C:30]([CH3:37])([CH3:29])[C:31]([OH:33])=[O:32])[CH:15]=[CH:16]2

Participants

5

Reactant 2

HCID 684322095-(3-(Benzyloxy)-7-bromo-1-fluoronaphthalen-2-yl)-1,2,5-thiadiazolidin-3-one 1,1-dioxideHCID 178419117HCID 178419117, compound

Product 1

HCID 177472975-[8-Fluoro-6-hydroxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-2,2-dimethyl-pentanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalyst

Procedure

This compound is prepared from 5-(3-benzyloxy-7-bromo-1-fluoronaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one and 2,2-dimethyl-pent-4-enoic acid-9-BBN similar to Example 8, Steps A and B, except in Step B, Pd(OH)2 is used to replace 10% Pd/C: Retention time=0.98 min (Method A); MS (M−H)−=423.

Sources & evidence

ORD record
ord-b9b19871356046f698b7e273e404be8d
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

Loading…