Triethylamine → (s)-Methyl 2-oxooxazolidine-4-carboxylate

HRID 2306076

反応式

HRID 2306076 の反応式
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.Cl[C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[O:20]=[C:18]1[NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:9])[CH2:7][O:8]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

生成物 1

HCID 385463(s)-Methyl 2-oxooxazolidine-4-carboxylate収率 93.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of L-serine methyl ester hydrochloride (3.063 kg) in dichloromethane (24.1 L) at 0° C. was treated with triethylamine (5.908 kg), stirred for 30 minutes, treated with triphosgene (1.949 kg) in dichloromethane (5.356 kg) over 6.5 hours, stirred for 45 minutes, treated with hexanes (12.23 kg), stirred for 55 minutes, and filtered with ethyl acetate (16.013 kg). The filtrate was concentrated to provide a 35% (w/w) solution of the desired product (93.5%, 98% ee) in ethyl acetate. 1H NMR (300 MHz, CDCl3) δ6.55 (br s, 1H), 4.62 (dd, J=9, 9 Hz, 1H), 4.53 (dd, J=4, 9 Hz, 1H), 4.45 (dd, J=4, 9 Hz, 1H), 3.83 (s, 3H).

後処理

  1. stirringstirred for 45 minutes
  2. stirringstirred for 55 minutes
  3. filtrationfiltered with ethyl acetate (16.013 kg)
  4. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-3e6062d7936f4eb09bd6363d41f1b71f
出典データセット
uspto-grants-2002_08
特許番号
US06441189B1

関連ノート

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