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

HRID 879275노트

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HRID 879275 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cd9da8a3ae59446eb71a84c9dabf3ba1
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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