Pyridine → methyl(4R)-3-(6-cyanohexyl)-2-oxo-1,3-oxazolidine-4-carboxylate

HRID 2215078

반응식

HRID 2215078 반응식
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][OH:12])#[N:2].N1C=CC=CC=1.[C:23](Cl)(Cl)=[O:24]>ClCCl.C1(C)C=CC=CC=1>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][O:12][C:23]1=[O:24])#[N:2]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 6371PhosgeneHCID 86606385methyl N-(6-cyanohexyl)-D-serinate

생성물 1

HCID 69659745methyl(4R)-3-(6-cyanohexyl)-2-oxo-1,3-oxazolidine-4-carboxylate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of amine 2-1 (620 mg) and pyridine (0.48 mL) in dichloromethane (10 mL) at 0° C. was added a solution of phosgene in toluene (1.72 mL, 1.9 M) and the mixture was stirred at the temperature for 1 h. The mixture was diluted with dichloromethane and washed with 1 N HCl and brine, and dried over Na2SO4. Filtration and concentration of the filtrate gave the crude product which was purified by chromatography. Eluting with 60% ethyl acetate in hexanes afforded the desired product 2-2 (560 mg). 1H NMR (400 MHz, acetone-d6): δ 4.61 (dd, 1H), 4.52 (t, 1H), 4.35 (dd, 1H), 3.80 (s, 3H), 3.48 (m, 1H), 3.15 (m, 1H), 2.47 (t, 2H), 1.75–1.35 (m, 8H).

후처리

  1. washwashed with 1 N HCl and brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and concentration of the filtrate
  4. customgave the crude product which
  5. customwas purified by chromatography
  6. washEluting with 60% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-82ec6ef3a7c1491798f57d621906b4a4
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109223B2

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