Dicyclohexylcarbodiimide → (3S-trans)-3-[[[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-4-methyl-1-(phenylmethoxy)-2-azetidinone

HRID 1156738

反応式

HRID 1156738 の反応式
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([OH:15])=O)=[O:10])[C:5](=[O:22])[C:4]1=[O:23])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:39][C@H:40]1[C@H:43]([CH3:44])[N:42]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]1=[O:53].C1(C)C(S([O-])(=O)=O)=CC=CC=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([NH:39][C@H:40]2[C@H:43]([CH3:44])[N:42]([O:45][CH2:46][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:41]2=[O:53])=[O:15])=[O:10])[C:5](=[O:22])[C:4]1=[O:23])[CH3:2]

参加物

8

反応物 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 3424274ToluenesulfonateHCID 4550893(R)-(-)-alpha-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]benzeneacetic acidHCID 13036842(3S-trans)-3-amino-4-methyl-1-(phenylmethoxy)-2-azetidinone

生成物 1

HCID 13036845(3S-trans)-3-[[[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-4-methyl-1-(phenylmethoxy)-2-azetidinone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A suspension of α-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]benzeneacetic acid (0.879 g) hydroxybenzotriazole (0.42 g), and dicyclohexylcarbodiimide (0.56 g), in dimethylformamide (15 ml) is stirred at 26° C. for one hour, at which point a solution of (3S-trans)-3-amino-4-methyl-1-(phenylmethoxy)-2-azetidinone, toluenesulfonate (0.95 g) and diisopropylethylamine (0.44 ml) in dimethylformamide (5 ml) is added. The reaction mixture is stirred at room temperature for about 16 hours, then poured into water (100 ml) and extracted with ethyl acetate (three 100 ml portions). The combined organic extracts are washed with water (three 100 ml portions) and aqueous sodium bicarbonate solution (one 100 ml portion), then dried over sodium sulfate and concentrated under reduced pressure to a semi-solid residue. Liquid chromatography (ethyl acetate) affords the desired product as a foam (0.599 g). Recrystallization from chloroform/isopropyl ether yields the title compound, melting point 100°-105° C.

後処理

  1. additionis added
  2. extractionextracted with ethyl acetate (three 100 ml portions)
  3. washThe combined organic extracts are washed with water (three 100 ml portions) and aqueous sodium bicarbonate solution (one 100 ml portion)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure to a semi-solid residue

出典と根拠

ORDレコード
ord-f18a8de656c042deb92a64063d2ef442
出典データセット
uspto-grants-1982_06
特許番号
US04337197

関連ノート

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