(R)-(-)-N-(2,3-Epoxypropyl)phthalimide → N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide

HRID 896633노트

반응식

HRID 896633 반응식
[O:1]1[CH2:3][C@H:2]1[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[SH:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CCO>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[S:16][CH2:3][C@H:2]([OH:1])[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15]

참가 물질

4

반응물 2

HCID 719415(R)-(-)-N-(2,3-Epoxypropyl)phthalimideHCID 178418395HCID 178418395, 화합물

생성물 1

HCID 10109719N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide수율 59%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of compound N-[(2R)-oxiran-2-ylmethyl]-phthalimide (21.1 g, 104 mmol) and 2-mercaptobenzothiazole (17.4 g, 104 mmol) in EtOH (600 mL) was heated to reflux for 16.5 h. The reaction was then cooled and concentrated under reduced pressure. The crude mixture was crystallized from ethanol and filtered to provide N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide (22.5 g, 59%) as a yellow solid. Data for N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide: 1H NMR (300 MHz, CDCl3) δ 7.88 (m, 2H), 7.75 (m, 4H), 7.45-7.26 (m, 2H), 5.18 (m, 1H), 4.42 (m, 1H), 4.08-3.88 (m, 2H), 3.61 (m, 1H), 3.42 (m, 1H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 16.5 h
  3. temperatureThe reaction was then cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was crystallized from ethanol
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-96dbfd0653a3425b944af13f4ba8c9ad
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919379B2

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