Tert-Butyl nitrite → HCID 58124950, compound

HRID 1971737Notes

Reaction equation

HRID 1971737 reaction equation
[C:1]([N:5]1[CH2:31][CH2:30][CH2:29][CH2:28][C:8]2[C:9]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([NH2:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:3])[CH3:2].C[Si]([N:37]=[N+:38]=[N-])(C)C.N(OC(C)(C)C)=O>C(#N)C.O>[C:1]([N:5]1[CH2:31][CH2:30][CH2:29][CH2:28][C:8]2[C:9]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([N:20]=[N+:37]=[N-:38])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 78378AzidotrimethylsilaneHCID 58124894HCID 58124894, compound

Product 1

HCID 58124950HCID 58124950, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.75 g of 20b in 40 ml of acetonitrile was added dropwise at 0° C. 0.54 g of trimethylsilyl azide, followed by 0.6 gr of tertbutyl nitrite. The reaction was stirred for ½ hr at ambient temperature, and then diluted with water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The remainder was chromatographed on silicagel (using a gradient of heptane/ethyl acetate as eluent), to provide 1.14 g of 20c. LCMS-ESI: [M+1] 476.17.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe remainder was chromatographed on silicagel (

Sources & evidence

ORD record
ord-5ba2a74e6dcf496bb307ea298e82d9f1
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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