tert-Butyldimethylsilyl chloride → HCID 58957864, compound

HRID 1849944Notes

Reaction equation

HRID 1849944 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:9][C:10]1([F:31])[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[O:12][C@H:11]1[N:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:20][C:19]1=[O:30]>N1C=CC=CC=1.O>[Si:1]([O:17][CH2:16][C@H:13]1[O:12][C@@H:11]([N:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:20][C:19]2=[O:30])[C:10]([F:31])([F:9])[C@@H:14]1[OH:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 15283218HCID 15283218, compound

Product 1

HCID 58957864HCID 58957864, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

tert-Butyldimethylsilyl chloride (737 mg, 4.89 mmol) was added to a solution of 8 (1.367 g, 4.08 mmol) in 8 mL of pyridine at 0° C. under N2. The reaction mixture was stirred overnight at RT, diluted with H2O, then extracted with EtOAc. The organic extract was washed with saturated aqueous CuSO4 solution, and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (1:1→3:1 EtOAc/Hexane) to give 1.4 g of 57 (white solid, 76% yield): 1H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1H), 8.14-8.16 (d, 1H), 7.14-7.16 (d, 1H), 6.42-6.43 (d, 1H), 6.20-6.23 (t, 1H), 4.17-4.23 (m, 3H), 3.98-4.08 (m, 2H), 3.87-3.90 (m, 1H), 1.25-1.28 (t, 3H), 0.94 (s, 9H), 0.14 (s, 6H).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous CuSO4 solution, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (1:1→3:1 EtOAc/Hexane)

Sources & evidence

ORD record
ord-c8f6a53764b94827953f77d85b6f927c
Source dataset
uspto-grants-2015_02
Patent number
US08956613B2

Reaction notes

Loading…