Boron tribromide → HCID 57777336, compound

HRID 660696Notes

Reaction equation

HRID 660696 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]#[C:16][CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][S:19]2(=[O:24])=[O:23])[CH:12]=[CH:11][C:10]=1[N:25]1[S:29](=[O:31])(=[O:30])[NH:28][C:27](=[O:32])[CH2:26]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[O:24]=[S:19]1(=[O:23])[CH2:20][CH2:21][CH2:22][CH:18]1[CH2:17][C:16]#[C:15][C:13]1[CH:12]=[CH:11][C:10]([N:25]2[S:29](=[O:31])(=[O:30])[NH:28][C:27](=[O:32])[CH2:26]2)=[C:9]([OH:8])[CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68839077HCID 68839077, compound

Product 1

HCID 57777336HCID 57777336, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-{2-benzyloxy-4-[3-(1,1-dioxotetrahydrothiophen-2-yl)-prop-1-ynyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one in methylene chloride (5 mL) is added BBr3 (0.35 mL of 1.0 M in methylene chloride) and the mixture is stirred at RT for 18 h. The solvent is removed under reduced pressure and the residue purified by preparative HPLC followed by lyophilization to give the title compound: (M−1)−=383; HPLC retention time=0.72 min. (Method A)

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-3c3750d73f5a458583b4beb1707135ed
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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