Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate

HRID 529548ノート

反応式

HRID 529548 の反応式
O=[CH:2][CH2:3][C@H:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:5].[C:14]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH2:17][CH3:18])=[O:15]>C1COCC1>[C:9]([O:8][C:7]([NH:6][C@H:4]([CH3:5])[CH2:3]/[CH:2]=[CH:19]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:13])([CH3:12])([CH3:11])[CH3:10]

参加物

4

反応物 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 25231755tert-butyl N-[(2R)-4-oxobutan-2-yl]carbamate

生成物 1

HCID 86706226(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate収率 80.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (R)-tert-butyl 4-oxobutan-2-ylcarbamate (1.54 g, 8.22 mmol) in THF (25 mL) at rt was added (carbethoxymethylene)triphenylphosphorane (6.30 g, 18.1 mmol) in portions. The resulting clear solution was stirred at rt under argon for 3 days. The reaction mixture was concentrated and the oily residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-60% EtOAc/Hex to give (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate (1.70 g, 6.61 mmol, 80% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 6.91 (dt, J=15.3, 7.5 Hz, 1H), 5.92-5.82 (m, 1H), 4.37 (s, 1H), 4.19 (q, J=7.1 Hz, 2H), 3.83 (s, 1H), 2.37 (t, J=6.6 Hz, 2H), 1.44 (s, 9H), 1.29 (t, J=7.1 Hz, 3H), 1.15 (d, J=6.7 Hz, 3H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe oily residue was purified
  3. washeluting with a gradient of 0-60% EtOAc/Hex

出典と根拠

ORDレコード
ord-a199d04452e44054a22ecb80c731ccf8
出典データセット
uspto-grants-2016_05
特許番号
US09346852B2

反応ノート

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