Ethanol → (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol

HRID 879275ノート

反応式

HRID 879275 の反応式
C([O:7][CH2:8][C@H:9]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20]([NH2:22])[S:21][C:17]=2[C:16]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=O)C(C)(C)C.CCO.C1COCC1>O>[NH2:22][C:20]1[S:21][C:17]2[C:16]([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)=[C:15]([C@H:9]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:8][OH:7])[C:24]([CH3:25])=[CH:23][C:18]=2[N:19]=1

参加物

5

反応物 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 86699790(S)-2-(2-Amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

生成物 1

HCID 86699791(S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol収率 62.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

A flask was charged with (S)-2-(2-Amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (2.15 g, 4.52 mmol), LiOH monohydrate (2.00 g, 47.4 mmol), H2O (4 mL), EtOH (absolute, 4.0 mL), and THF (8.0 mL). The reaction was placed under N2 and heated to 100° C. After 2 h, the reaction was cooled to 23° C., diluted with H2O, and extracted with EtOAc several times. The combined organic phases were dried (Na2SO4), filtered, and concentrated. The residue was treated with benzene and purified via chromatography on silica gel (80 g “gold” ISCO column; Hex/EtOAc) giving (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol (1.10 g, 62% yield). LCMS-ESI+: calc'd for C20H23ClN2O2S: 391.1 and 393.1 (M+H+); found: 391.2 and 393.2 (M+H+). 1H-NMR: 400 MHz, (CDCl3) δ: 7.49-7.41 (m, 2H), 7.36-7.32 (m, 2H), 7.20 (d, J=7.3 Hz, 1H), 5.39 (s, broad, 2H), 4.52-4.50 (m, 1H), 3.85-3.70 (m, 2H), 2.63 (s, 3H), 0.99 (s, 9H).

後処理

  1. temperaturethe reaction was cooled to 23° C.
  2. extractionextracted with EtOAc several times
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe residue was treated with benzene
  7. custompurified via chromatography on silica gel (80 g “gold” ISCO column; Hex/EtOAc)

出典と根拠

ORDレコード
ord-cd9da8a3ae59446eb71a84c9dabf3ba1
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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