(E)-2,2-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pent-4-en-1-ol → 5-[1-Fluoro-3-hydroxy-7-(5-hydroxy-4,4-dimethylpentyl)-naphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 889264Notes

Reaction equation

HRID 889264 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]([CH3:45])([CH2:33]/[CH:34]=[CH:35]/B1OC(C)(C)C(C)(C)O1)[CH2:31][OH:32]>>[F:20][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([CH2:35][CH2:34][CH2:33][C:30]([CH3:45])([CH3:29])[CH2:31][OH:32])[CH:13]=2)[CH:18]=[C:9]([OH:8])[C:10]=1[N:21]1[S:25](=[O:26])(=[O:27])[NH:24][C:23](=[O:28])[CH2:22]1

Participants

3

Reactant 2

HCID 68431549(E)-2,2-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pent-4-en-1-olHCID 684322095-(3-(Benzyloxy)-7-bromo-1-fluoronaphthalen-2-yl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 177472965-[1-Fluoro-3-hydroxy-7-(5-hydroxy-4,4-dimethylpentyl)-naphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Procedure

The title compound is prepared analogously to Example 9, Steps A and B, starting from 5-(3-benzyloxy-7-bromo-1-fluoronaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one and (E)-2,2-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pent-4-en-1-ol, Retention time=1.16 min (Method A); MS (M−H)−=409.

Sources & evidence

ORD record
ord-d7487522c4954bf4bb874da557504064
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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