Boron tribromide → HCID 57777461, compound

HRID 660740Notes

Reaction equation

HRID 660740 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[S:17][CH:18]=[CH:19][N:20]=2)[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[S:17][CH:18]=[CH:19][N:20]=2)[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68838984HCID 68838984, compound

Product 1

HCID 57777461HCID 57777461, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a suspension of 5-(2-benzyloxy-4-thiazol-2-ylmethylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (20 mg, 0.05 mmol) in CH2Cl2 (5 mL) at −10° C. is added BBr3 (0.2 mL, 1.0 M in CH2Cl2) and the yellow mixture is stirred at −10° C. for 30 min. The reaction is quenched with water and the aqueous layer is neutralized to pH=7 with 1N NaOH. The aqueous layer is then concentrated and the residue is purified by reverse phase HPLC (CH3CN/water/0.1% TFA) to give the title compound as a light yellow solid: 1H NMR (MeO4.16 (s, 2H), 4.18 (s, 2H), 6.68 (d, J=8 Hz, 1H), 7.73 (s, 1H), 7.28 (d, J=8 Hz, 1H), 7.34 (d, J=4 Hz, 1H) 7.56 (d, J=4 Hz, 1H); (M−1)−=324.

Workup

  1. customThe reaction is quenched with water
  2. concentrationThe aqueous layer is then concentrated
  3. customthe residue is purified by reverse phase HPLC (CH3CN/water/0.1% TFA)

Sources & evidence

ORD record
ord-e8063eecc3ac4e318ff7cbc0e055be2d
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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