Chlorotrimethylsilane → HCID 68593660、化合物

HRID 2191064ノート

反応式

HRID 2191064 の反応式
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH2:16][CH:17]([P:26](=[O:29])([OH:28])[OH:27])S(C2C=CC=CC=2)=O)[CH:13]([F:30])[CH:12]1[OH:31].C(N(CCCC)CCCC)CCC.C[Si](Cl)(C)C>CN(C=O)C>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH:16]=[CH:17][P:26](=[O:27])([OH:28])[OH:29])[CH:13]([F:30])[CH:12]1[OH:31]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 7622TributylamineHCID 68593093HCID 68593093、化合物

生成物 1

HCID 68593660HCID 68593660、化合物収率 31.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

Compound 49.4 (147 mg, 0.31 mmol) was dissolved in anhydrous DMF, treated with tributylamine (1.49 mL, 6.24 mmol) and TMSCl (0.79 mL, 6.24 mmol). The mixture was heated to 130° C. for 4 h and then cooled to rt. The reaction was quenched with water and stirred at rt for another 2 h. The mixture was concentrated under reduced pressure and the residue was washed with acetonitrile. The acetonitrile washes were discarded and the residue was dissolved in water, subjected to a reverse phase HPLC to give compound 49.5 (34 mg, 24% yield). 1H NMR (D2O, 300 MHz): δ 4.91-5.17 (m, 3H), 5.92-5.95 (m, 1H), 6.07-6.59 (m, 2H), 8.37 (s, 1H). 31PNMR: 11.82 ppm. LRMS [M−H]− C11H13FN5O5P requires 344.1. Found 344.1.

後処理

  1. temperaturecooled to rt
  2. customThe reaction was quenched with water
  3. concentrationThe mixture was concentrated under reduced pressure
  4. washthe residue was washed with acetonitrile
  5. dissolutionthe residue was dissolved in water

出典と根拠

ORDレコード
ord-168fe75088b64fe89996c55f9f50244d
出典データセット
uspto-grants-2012_12
特許番号
US08324179B2

反応ノート

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