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

HRID 2118560

反応式

HRID 2118560 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

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 6344Dichloromethane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, J7.Hz, 2H), 3.58-3.68 (m.2H), 3.93-4.23 (complex m, together 3H), 5.59-5.84 (complex m, together 1 H) (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-7fd4311c308e40b48b0f9f8db0de0d51
出典データセット
uspto-grants-1987_07
特許番号
US04678782

関連ノート

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