Water → Bexagliflozin

HRID 1175256노트

반응식

HRID 1175256 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][CH:41]2[CH2:43][CH2:42]2)(=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][CH:41]2[CH2:43][CH2:42]2)=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 44580555Bms-5119262회HCID 59557773Toluene-4-sulfonic acid 2-cyclopropoxy-ethyl ester

생성물 1

HCID 25195624Bexagliflozin

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (intermediate D1) (30 mg, 0.08 mmol) in anhydrous DMF (1 mL) were added 2-cyclopropoxyethyl 4-methylbenzenesulfonate (intermediate BP) (20 mg, 0.08 mmol) and Cs2CO3 (52 mg, 0.16 mmol). The mixture was stirred at room temperature for 12 h. Then the reaction mixture was poured into water, extracted with EA, washed with brine, dried with anhydrous Na2SO4 and concentrated to an oil. The oil was purified by preparative HPLC to obtain compound BQ (11 mg) as a colorless oil. 1H NMR (CD3OD): δ 7.30 (m, 3H), 7.11 (d, J=8.8 Hz, 2H), 6.82 (d, J=8.8 Hz, 2H), 4.13 (m, 5H), 3.85 (m, 3H), 3.81 (m, 1H), 3.40 (m, 4H), 3.30 (m, 1H), 0.52 (m, 4H); MS ESI (m/z) 465 (M+H)+, calc. 464.

후처리

  1. extractionextracted with EA
  2. washwashed with 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 BQ (11 mg) as a colorless oil

출처 및 근거

ORD 기록
ord-c4773b3c18064a1c923c2950a2431d32
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838499B2

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