Boron tribromide → HCID 57777311, compound

HRID 660813Notes

Reaction equation

HRID 660813 reaction equation
[K].[C:2]1([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH2:18]3)=[C:13]([O:25]CC3C=CC=CC=3)[CH:12]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[C:2]1([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH2:18]3)=[C:13]([OH:25])[CH:12]=2)(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68838679HCID 68838679, compound

Product 1

HCID 57777311HCID 57777311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-benzenesulfonyl-2-benzyloxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium in CH2Cl2 (5 mL), cooled in an ice/salt bath, is added dropwise BBr3 (4.8 mL, 1M in CH2Cl2). The mixture is stirred for 30 min then is quenched with water, basified with potassium carbonate, and separated. The aqueous layer is washed with ether, then lyophilized, and purified by preparative HPLC to afford the title compound as an amorphous solid: mp=126-180° C.; 1H NMR (DMSO-d6) δ 10.89 (br s, 1H), 7.93 (d, J=7.0 Hz, 2H), 7.66 (m, 4H), 7.42 (m, 2H), 4.56 (s, 2H); (M−1)−=367.

Workup

  1. customthen is quenched with water
  2. customseparated
  3. washThe aqueous layer is washed with ether
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8d8d27bac62441d0963a1a1f638a1c70
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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