Chlorotrimethylsilane → HCID 135903213, 화합물

HRID 2191051노트

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HRID 2191051 반응식
[NH2:1][C:2]1[NH:3][C:4](=[O:32])[C:5]2[N:6]=[CH:7][N:8]([C@@H:11]3[O:15][C@H:14]([CH2:16][CH:17]([P:26](=[O:29])([OH:28])[OH:27])S(C4C=CC=CC=4)=O)[C@@H:13]([F:30])[C@H:12]3[OH:31])[C:9]=2[N:10]=1.C(N(CCCC)CCCC)CCC.C[Si](Cl)(C)C>CN(C=O)C>[NH2:1][C:2]1[NH:3][C:4](=[O:32])[C:5]2[N:6]=[CH:7][N:8]([C@@H:11]3[O:15][C@H:14](/[CH:16]=[CH:17]/[P:26](=[O:27])([OH:29])[OH:28])[C@@H:13]([F:30])[C@H:12]3[OH:31])[C:9]=2[N:10]=1

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 7622TributylamineHCID 136351465HCID 136351465, 화합물

생성물 1

HCID 135903213HCID 135903213, 화합물수율 73.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

Compound 35.18 (12 mg, 0.025 mmol) was dissolved in anhydrous DMF (4 mL), treated with tributylamine (0.12 mL, 0.5 mmol) and TMSCl (0.063 mL, 0.5 mmol). The mixture was heated to 130° C. for 4 h, cooled to r.t., and then quenched with 2 mL water. The mixture was stirred at r.t for another 2 h and then the solvent was removed under reduced pressure. The residue was washed with 3×20 mL acetonitrile to remove TBA and TMSOH. The acetonitrile washes were discarded and the solid was dissolved in water, subjected to a reverse phase HPLC to give compound 35.19 (6.6 mg, 73% yield). 1HNMR (D2O, 300 MHz) δ 8.40 (s, 1H), 6.57 (m, 1H), 6.13 (t, 1H), 5.92 (d, 1H), 4.90-5.20(m, 3H). 31PNMR (D2O, 300 MHz): 11.815 ppm. LRMS (ESI) MH+ C11H13FN5O6P requires 362.1. Found 362.0.

후처리

  1. temperaturecooled to r.t.
  2. customquenched with 2 mL water
  3. customthe solvent was removed under reduced pressure
  4. washThe residue was washed with 3×20 mL acetonitrile
  5. customto remove TBA and TMSOH
  6. dissolutionthe solid was dissolved in water

출처 및 근거

ORD 기록
ord-3637144873a04897a10bd924a1183a68
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324179B2

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