Chlorotrimethylsilane → HCID 67336616, compound

HRID 335378Notes

Reaction equation

HRID 335378 reaction equation
Cl[Si](C)(C)C.[NH2:6][C:7]1[C:8]2[NH:15][CH:14]=[C:13]([CH2:16][N:17]([CH:35]([CH2:38][OH:39])[CH2:36][OH:37])[C:18](=[O:34])[O:19][CH2:20][CH:21]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:27]4[C:22]3=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:9]=2[N:10]=[CH:11][N:12]=1.[C:40](Cl)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>N1C=CC=CC=1>[C:40]([NH:6][C:7]1[C:8]2[NH:15][CH:14]=[C:13]([CH2:16][N:17]([CH:35]([CH2:36][OH:37])[CH2:38][OH:39])[C:18](=[O:34])[O:19][CH2:20][CH:21]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[C:28]4[C:33]3=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:9]=2[N:10]=[CH:11][N:12]=1)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 67335727HCID 67335727, compound

Product 1

HCID 67336616HCID 67336616, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Chlorotrimethylsilane (810 μL, 6.3 mmol) was added to a solution of 7 (194 mg, 0.42 mmol) in dry pyridine. After 30 min benzoyl chloride (172 μL, 1.48 mmol) was added and the solution was stirred overnight. The reaction was quenched by the addition of water and concentrated to dryness. The residue was taken up in dichloromethane (10 mL), washed with water, concentrated, stirred for 5 min in methanolic ammonia (7N) and concentrated again. Chromatography of the residue on silica gel eluted with 4% methanol in dichloromethane gave the title compound as a colourless, amorphous solid (160 mg, 2.84 mmol, 67%). ESI-MS+, found 564.2245, calc. for C32H30N5O5 [M+H]+ 564.2245.

Workup

  1. customThe reaction was quenched by the addition of water
  2. concentrationconcentrated to dryness
  3. washwashed with water
  4. concentrationconcentrated
  5. stirringstirred for 5 min in methanolic ammonia (7N)
  6. concentrationconcentrated again
  7. washChromatography of the residue on silica gel eluted with 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-7c327dfa74c441f48864a835a852b54f
Source dataset
uspto-grants-2014_11
Patent number
US08884000B2

Reaction notes

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