Benzyl Alcohol → Benzyl 2-amino-3-(3-hydroxyphenyl)propanoate

HRID 1397872노트

반응식

HRID 1397872 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH:13]1[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([CH2:20][C@H:21]([NH2:25])[C:22](O)=[O:23])[CH:14]=1>CCOC(C)=O>[NH2:25][CH:21]([CH2:20][C:15]1[CH:14]=[CH:13][CH:18]=[C:17]([OH:19])[CH:16]=1)[C:22]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:23]

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 24386Thionyl ChlorideHCID 6950578L-m-tyrosine

생성물 1

HCID 14888692Benzyl 2-amino-3-(3-hydroxyphenyl)propanoate수율 59%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
-5 °C

실험 절차

To 10 mL of benzyl alcohol at −5° C. was added, with stirring, 0.2 mL of SOCl2 slowly. The clear colorless solution was cooled to −5° C. and 490 mg of meta-Tyrosine was added. After 5 min, the resulting solution was heated to 120° C. overnight. 100 ml of AcOEt are added. The organic phase are washed with saturated NaHCO3 and brine then dried over Na3SO4, filtered and concentrated to afford 170 as a white solid (430 mg, 59%). 1H NMR (DMSO): δ 1.90 (s, 3H), 2.87 (dd, 1H, J=13.1, 6.5 Hz), 2.94 (dd, 1H, J=13.1, 6.5 Hz), 3.73 (t, 1H, J=6.5 Hz), 5.19 (s, 2H), 6.70 (d, 1H, J=7.7 Hz), 6.75 (s, 1H), 7.17 (t, 1H, J=7.7 Hz), 7.41 (d, 1H, J=7.0 Hz), 7.48 (m, 5H), 9.37 (s, 1H).

후처리

  1. temperaturethe resulting solution was heated to 120° C. overnight
  2. washThe organic phase are washed with saturated NaHCO3 and brine
  3. dry with materialthen dried over Na3SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7cfaaadc206041adb45e7b309a17a488
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901295B2

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