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

HRID 896633ノート

反応式

HRID 896633 の反応式
[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]

参加物

4

反応物 2

HCID 719415(R)-(-)-N-(2,3-Epoxypropyl)phthalimideHCID 178418395HCID 178418395、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-96dbfd0653a3425b944af13f4ba8c9ad
出典データセット
uspto-grants-2005_07
特許番号
US06919379B2

反応ノート

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