Chlorotrimethylsilane → HCID 68593660, 화합물

HRID 2191064노트

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HRID 2191064 반응식
[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]

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 7622TributylamineHCID 68593093HCID 68593093, 화합물

생성물 1

HCID 68593660HCID 68593660, 화합물수율 31.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-168fe75088b64fe89996c55f9f50244d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324179B2

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