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

HRID 751673ノート

反応式

HRID 751673 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b5521b9e8fce4ff29543c84c4e48f37b
出典データセット
uspto-grants-2008_07
特許番号
US07405210B2

反応ノート

読み込み中…