홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium borohydride → (R)-N-naphthalene-2-sulfonyl (3-hydroxy-cyclohepty)glycine ethyl ester

HRID 77330
노트
인쇄 미리보기

반응식

HRID 77330 반응식
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22](=[O:27])[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8])[CH3:2].[BH4-].[Na+]>O1CCCC1CCO>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]([OH:27])[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:8])=[O:9])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86653278(R)-N-naphthalene-2-sulfonyl (3-oxo-cyclohepty)glycine ethyl ester

생성물 1

HCID 86653277(R)-N-naphthalene-2-sulfonyl (3-hydroxy-cyclohepty)glycine ethyl ester수율 85%

시약·촉매·용매 1

HCID 119895722-(Oxolan-2-yl)ethan-1-ol용매

반응 조건

온도
0 °C

실험 절차

To a solution of (R)—N-naphthalene-2-sulfonyl (3-oxo-cyclohepty)glycine ethyl ester (1.05 g, 2.61 mmol) in tetrahydrofuran-ethanol (20 mL, 1:1) at 0° C. is added sodium borohydride (0.147 g, 3.88 mmol) and the reaction is stirred at 0° C. for 1 hour. The reaction was quenched at 0° C. with citric acid (10% aqueous), and the solvents were removed in vacuo. The residue was dissolved in water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by column chromatography (50% hexanes-ethyl acetate) to afford the title compound as a white solid (0.90 g, 85% yield). LCMS (m/z): 406.14 (M+1), 404.13 (M−1).

후처리

  1. customThe reaction was quenched at 0° C. with citric acid (10% aqueous)
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (50% hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-48ea1697e4ac4b93ba100314d0fe3485
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841291B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트