Water → HCID 57777307, compound

HRID 660729Notes

Reaction equation

HRID 660729 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH:12]=[CH:11][C:10]=1[N:20]1[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]1)C1C=CC=CC=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:8][C:9]1[CH:14]=[C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH:12]=[CH:11][C:10]=1[N:20]1[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 68839035HCID 68839035, compound

Product 1

HCID 57777307HCID 57777307, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a suspension of 5-(2-benzyloxy-4-thiazol-2-yl-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (50 mg, 0.125 mmol) in CH2Cl2 (5 mL) at −10° C. is added BBr3 (1.0M in CH2Cl2, 0.68 mL) dropwise. The yellow mixture is stirred at −10° C. for 30 min. Water is added to the reaction mixture and the aqueous layer is separated and neutralized with 1N NaOH. The water is removed under reduced pressure and the residue is purified by reverse phase HPLC (MeCN/water/0.1% TFA) to afford the title compound as a light yellow solid: 1H NMR (D24.45 (s, 1H), 7.48-7.54 (m, 3H), 7.61 (d, J=4 Hz, 1H), 7.85 (d, J=4 Hz, 1H); (M−1)−=310.

Workup

  1. customthe aqueous layer is separated
  2. customThe water is removed under reduced pressure
  3. customthe residue is purified by reverse phase HPLC (MeCN/water/0.1% TFA)

Sources & evidence

ORD record
ord-6a121fb119844317984cd0d82be03717
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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