Water → 2-(5-Bromo-1,3-thiazol-2-yl)-1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol

HRID 1039940

Reaction equation

HRID 1039940 reaction equation
[Si:1]([O:8][CH2:9][C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)([OH:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:18]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:18][C:15]1[S:14][C:13]([C:10]([OH:12])([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])=[N:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 674295761-{[Tert-butyl(dimethyl)silyl]oxy}-2-(1,3-thiazol-2-yl)propan-2-ol

Product 1

HCID 674313722-(5-Bromo-1,3-thiazol-2-yl)-1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-olYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Step 1 (364 mg, 1.331 mmol) was dissolved in DMF (2 ml). N-bromosuccinimide (284 mg, 1.597 mmol) was added, and the solution was maintained 2 h at rt. Water was added and the mixture extracted with EtOAc (3×). The combined organics were dried over Na2SO4 and concentrated in vacuo. Purification via silica gel column chromatography (0%-10% EtOAc:hexanes) afforded 2-(5-bromo-1,3-thiazol-2-yl)-1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol (104 mg, 22%) as a white solid. MS ESI: [M+H]+ m/z 352, 354.

Workup

  1. extractionthe mixture extracted with EtOAc (3×)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification via silica gel column chromatography (0%-10% EtOAc:hexanes)

Sources & evidence

ORD record
ord-61c43b45f1694c26af7754fe5ff2a664
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Linked notes

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