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

HRID 2306076

반응식

HRID 2306076 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3e6062d7936f4eb09bd6363d41f1b71f
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06441189B1

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