Lithium tri-s-butylborohydride → HCID 58746935, compound

HRID 724727Notes

Reaction equation

HRID 724727 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][C@H:21]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:22]2[N:23]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:25][N:26]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:12](=[O:14])(=[O:13])[N:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:10](=[O:19])[CH:9]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][C@H:21]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:22]2[N:23]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:39])([CH3:38])[CH3:40])[C:24]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:25][N:26]=2)[CH:5]=[CH:6][C:7]=1[CH:8]1[S:12](=[O:13])(=[O:14])[N:11]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:10](=[O:19])[CH2:9]1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 58746634tert-Butyl [(1S)-2-[3-bromo-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate

Product 1

HCID 58746935HCID 58746935, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl [(1S)-2-[3-bromo-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate (70 mg, 92.1 μmol) and tetrahydrofuran (20 mL) was stirred at −78° C. After stirring for 5 min, 1.0 M L-selectride in tetrahydrofuran (92 μL) was added dropwise. The reaction was quenched with glacial acetic acid (0.7 mL). The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (65 mg, 83%). MF=C35H49BrN4O6SSi; LCMS found for C35H50BrN4O6SSi(M+H)+: m/z=761.

Workup

  1. customThe reaction was quenched with glacial acetic acid (0.7 mL)
  2. additionThe reaction was diluted with water
  3. extractionextracted with ethyl acetate three times
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-7993c3a7e662492ba2d5be6e4b0d1be8
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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