Phenethylamine → HCID 14444045, 화합물

HRID 1978284노트

반응식

HRID 1978284 반응식
O=[O+][O-].[CH2:4]([O:11][C:12](=[O:47])[CH2:13][CH:14]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:15](=[O:38])C(C#N)=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:48]([NH2:56])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C(Cl)Cl>[NH:39]([C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[C@H:14]([C:15]([NH:56][CH2:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:38])[CH2:13][C:12](=[O:47])[O:11][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 1001PhenethylamineHCID 24823OzoneHCID 54318947HCID 54318947, 화합물

생성물 1

HCID 14444045HCID 14444045, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

Ozone gas was bubbled through a solution of 5 (606 mg, 1 mmol) in CH2Cl2 (20 mL) cooled to −78° C. until its blue color persists within the solution. The excess ozone was purged using argon and phenethylamine (181 mg, 189 μL, 1.5 mmol) was added. The resulting solution was stirred at −78° C. for 1 h and then allowed to warm to r.t. The solvent was removed under reduced pressure and the residue chromatographed on silica gel (0-30% ethyl acetate in hexane) to yield the product as a clear oil which was then recrystallized from ether/hexane (145 mg, 32%): mp 132-134° C.; 1H NMR (CDCl3) δ1.43 (s, 9H, Boc CH3's), 2.81 (t, 2H, NHCH2—CH2—Ph), 3.12 (dd, 1H, 1 of CH2—CO2Bzl), 3.44 (dd, 1H, 1 of CH2—CO2Bzl), 3.55 (t, 2H, NH—CH2—CH2Ph), 5.10 (s, 2H, benzyl CH2), 5.13 (m, 1H, α-CH), 5.51 (d, 1H, urethane NH), 6.92 (br, 1H, amide NH), 7.20 (m, 5H, phenethyl aromatic CH's), 7.30 (m, 5H, benzyl aromatic CH's); FABMS (calculated for C25H31N2O6, 455.2182) m/e 455.2146 (M++1).

후처리

  1. customThe excess ozone was purged
  2. additionwas added
  3. temperatureto warm to r.t
  4. customThe solvent was removed under reduced pressure
  5. customthe residue chromatographed on silica gel (0-30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-130deaf46a5d4cc0a753cf0fae546f28
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235929B1

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