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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Iodoethane → (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

HRID 1258821
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HRID 1258821 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:21]=[CH:22][C:23]2[O:28][CH2:27][CH2:26][NH:25][C:24]=2[CH:29]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:36](I)[CH3:37]>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]2[O:28][CH2:27][CH2:26][N:25]([CH2:36][CH3:37])[C:24]=2[CH:29]=1
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참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 52913742(2S,3R,4R,5S,6R)-2-[4-chloro-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

생성물 1

HCID 52914178(2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol수율 19.3%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

반응 조건

온도
20 °C

실험 절차

To a stirred solution of (2S,3R,4R,5S,6R)-2-[4-chloro-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (0.1 g, 0.23 mmol) in DMF (2 mL) was added potassium carbonate (0.065 g, 0.47 mmol, ethyl iodide (0.028 mL, 0.35 mmol) and stirred the solution at 20° C. for 2 h. Reaction mixture was quenched by the addition of water (2 mL), extracted with dichloromethane (3×5 mL). The organic layer was washed with water (5 mL), brine (5 mL), dried over sodium sulfate, concentrated and purified by preparative HPLC to furnish (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (20 mg).

후처리

  1. customReaction mixture
  2. customwas quenched by the addition of water (2 mL)
  3. extractionextracted with dichloromethane (3×5 mL)
  4. washThe organic layer was washed with water (5 mL), brine (5 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-906b83dff5084bd3b527a93bff76cd5d
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466114B2

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