Water → HCID 25196961, 화합물

HRID 425070노트

반응식

HRID 425070 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.CC1C=CC(S(O[CH2:38][CH2:39][O:40][CH2:41][C:42]([F:45])([F:44])[F:43])(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:38][CH2:39][O:40][CH2:41][C:42]([F:45])([F:44])[F:43])=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 220332952-(2,2,2-Trifluoroethoxy)ethyl p-toluenesulfonateHCID 44580555Bms-5119262회

생성물 1

HCID 25196961HCID 25196961, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (intermediate D1) (200 mg) in anhydrous DMF were added 2-(2,2,2-trifluoroethoxy)ethyl 4-methylbenzenesulfonate (intermediate BS) (1.5 eq) and Cs2CO3 (2 eq). The mixture was stirred at room temperature for 12 h, after which LC-MS showed the reaction was complete. The reaction mixture was poured into water, extracted with EA, washed with water and brine, and then dried with anhydrous Na2SO4 and concentrated to an oil. The oil was purified by preparative-HPLC to obtain compound BT (117 mg). 1H NMR (CD3OD, 400 MHz): δ 7.32 (m, 3H), 7.11 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 4.62 (s, 2H), 4.08˜4.12 (m, 3H), 4.02˜4.05 (m, 3H), 4.00˜3.94 (m, 2H), 3.90˜3.87 (m, 1H), 3.72˜3.68 (m, 1H), 3.46˜3.39 (m, 3H), 3.30˜3.27 (m, 1H); MS ESI (m/z) 507 (M+H)+, calc. 506.

후처리

  1. extractionextracted with EA
  2. washwashed with water and brine
  3. dry with materialdried with anhydrous Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe oil was purified by preparative-HPLC
  6. customto obtain compound BT (117 mg)

출처 및 근거

ORD 기록
ord-90ca94cc1cbc4f29bfd355456f8116d4
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106021B2

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