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Boron trifluoride etherate → Dapagliflozin

HRID 718218
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인쇄 미리보기

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HRID 718218 반응식
C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C@@:24]2(OC)[C@H:29]([OH:30])[C@@H:28]([OH:31])[C@H:27]([OH:32])[C@@H:26]([CH2:33][OH:34])[O:25]2)=[CH:20][C:19]=1[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH3:46])=[CH:40][CH:39]=1>ClCCl.C(#N)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C@H:24]2[C@H:29]([OH:30])[C@@H:28]([OH:31])[C@H:27]([OH:32])[C@@H:26]([CH2:33][OH:34])[O:25]2)=[CH:20][C:19]=1[CH2:37][C:38]1[CH:39]=[CH:40][C:41]([O:44][CH2:45][CH3:46])=[CH:42][CH:43]=1
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참가 물질

6

반응물 3

HCID 8000Boron trifluoride etherate2회HCID 12052Triethylsilane2회HCID 24807437Methyl 1-C-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-alpha-D-glucopyranoside2회

생성물 1

HCID 9887712Dapagliflozin

시약·촉매·용매 2

HCID 6342Acetonitrile용매3회
HCID 6344
Dichloromethane
용매
3회

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온도
-22.5 °C

실험 절차

To a 100 mL 3-neck flask equipped with magnetic stirrer and under argon atmosphere was added dichloromethane (7.0 mL), acetonitrile (7.0 mL) and triethylsilane (5.09 mL, 31.9 mmol) successively at room temperature. The above mixture was cooled to −20 to −25° C. and BF3.Et2O (3.03 mL, 23.9 mmol) was added in one portion. Another 100 mL flask was charged with crude (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (3.5 g, 7.97 mmol), dichloromethane (7.0 mL) and acetonitrile (7.0 mL), and the resulting mixture was shaking for 20 min at ambient temperature until a clear solution was obtained. Under an atmosphere of nitrogen, the (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol solution in dichloromethane and acetonitrile was transferred to an addition funnel and was slowly added to the solution of BF3-Et2O and triethylsilane over a period of 1 h while keeping the internal temperature between −15 to −20° C. After the addition was completed, the mixture was stirred at a temperature between −15 to −20° C.

후처리

  1. customTo a 100 mL 3-neck flask equipped with magnetic stirrer and under argon atmosphere
  2. customwas obtained
  3. custombetween −15 to −20° C
  4. additionAfter the addition
  5. stirringthe mixture was stirred at a temperature between −15 to −20° C.

출처 및 근거

ORD 기록
ord-db92ed607785465e83ee0c2960067d77
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193751B2

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