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

HRID 2118560

반응식

HRID 2118560 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-7fd4311c308e40b48b0f9f8db0de0d51
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04678782

연결된 노트

불러오는 중…