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

HRID 2215078

反応式

HRID 2215078 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-82ec6ef3a7c1491798f57d621906b4a4
出典データセット
uspto-grants-2006_09
特許番号
US07109223B2

関連ノート

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