Triethylamine → (S)-4-(4-Fluorobenzyl)oxazolidine-2,5-dione

HRID 751673노트

반응식

HRID 751673 반응식
C([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C(OCC)(=O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C@H:9]2[C:10](=[O:12])[O:11][C:6](=[O:5])[NH:8]2)=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine

생성물 1

HCID 59753664(S)-4-(4-Fluorobenzyl)oxazolidine-2,5-dione

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2(S)-tert-butoxycarbonylamino-3-(4-fluorophenyl)propionic acid (1.5 g, 5.29 mmol) in ethyl acetate (100 mL) under an argon atmosphere was added triphosgene (628 mg, 2.12 mmol). To the solution was added triethylamine (0.8 mL 5.76 mmol,) over 1 min, and the reaction stirred for 72 h at rt. The reaction mixture was filtered, and the filtrate concentrated in vacuo to yield an oily residue. The crude material was crystallised from cold dichloromethane and petroleum ether to give the title compound. δH (CD3OD): 7.20 (2H, m), 7.10 (2H, m), 5.86 (1H, s, (NH)), 4.58 (1H, s), 3.33–3.23 (2H, m), 3.11–3.00 (1H, m).

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto yield an oily residue
  4. customThe crude material was crystallised from cold dichloromethane and petroleum ether

출처 및 근거

ORD 기록
ord-b5521b9e8fce4ff29543c84c4e48f37b
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405210B2

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