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Pyridine → 3[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-3-formamido-4-methylazetidin-2-one

HRID 246868
ノート
印刷プレビュー

反応式

HRID 246868 の反応式
[NH2:1][C:2]1([NH:8][C:9](=[O:30])[CH:10]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH3:27])[C:22](=[O:28])[C:21]2=[O:29])=[O:19])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]([CH3:6])[NH:4][C:3]1=[O:7].N1C=CC=CC=1.[C:37](OC=O)(=[O:39])C>ClCCl>[CH2:26]([N:23]1[CH2:24][CH2:25][N:20]([C:18]([NH:17][CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]([NH:8][C:2]2([NH:1][CH:37]=[O:39])[CH:5]([CH3:6])[NH:4][C:3]2=[O:7])=[O:30])=[O:19])[C:21](=[O:29])[C:22]1=[O:28])[CH3:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 75269Acetic-formic anhydrideHCID 201628613-Amino-3[2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methylazetidin-2-one

生成物 1

HCID 201628873[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-3-formamido-4-methylazetidin-2-one収率 86.2%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A solution of the amine (62) (87 mg) and pyridine (33 mg) in dry dichloromethane (2 ml) was treated with formic acetic anhydride (40 mg) for 24 hour after which time the solvent was removed in vacuo. Dry dioxan was added and solution re-evaporated (×3). Silica gel column chromatography of the residue gave the title compound (63) (80 mg) as a white powder, νmax. (Nujol) 3500, 3250, 1770, 1710, 1670, and 1500 cm-1, δ[(CD3)2CO]0.88, 0.96, 1.00 and 1.03 (each d, J 6.5 Hz, together 3H) (irradiation at 4.00 caused the signals centered at 0.88 and 0.96 to collapse to 2×s), 1.16 (t, J7 Hz, 3H), 3.49 (q, J 7 .Hz, 2H), 3.58-3.68 (m. 2H), 3.93-4.23 (complex m, together 3H), 5.59-5.84 (complex m, together 1H) (collapses to 4×s at 5.65, 5.69, 5.76 and 5.80 upon irradiation at 10.0), 7.25-7.80 (complex m, together 6H) (simplifies on exchange with D2O to a m at 7.25-7.56), 7.97-8.86 (complex m, together 3H) (simplifies to 4×s at 8.03, 8.11, 8.24, and 8.48 on exch.), 9.90-10.05 (m, 1H, exch).

後処理

  1. customwas removed in vacuo
  2. additionDry dioxan was added
  3. customsolution re-evaporated (×3)

出典と根拠

ORDレコード
ord-747ac32492224600bc2ac6e4b6a6203e
出典データセット
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04704385

反応ノート

読み込み中…

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