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Acetonitrile → HCID 131730036、化合物

HRID 2067716
ノート
印刷プレビュー

反応式

HRID 2067716 の反応式
O(P(OC1C=CC=CC=1)(O[C:11]1[C@H:17]([CH3:18])[C@@H:16]2[N:13]([C:14](=[O:22])[C@@H:15]2[C@H:19]([OH:21])[CH3:20])[C:12]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])=O)C1C=CC=CC=1.C(N([CH:49]([CH3:51])[CH3:50])CC)(C)C.C([S:55][C@@H:56]1[CH2:60][N:59]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[C@H:58]([C:68]([OH:70])=O)[CH2:57]1)(=O)C.[C:71]([O:74]CC)(=O)[CH3:72].C(#[N:79])C>>[CH:68]([C@:58]1([NH:79][CH2:72][C:71]2[O:74][CH:51]=[CH:49][CH:50]=2)[CH2:57][C@H:56]([S:55][C:11]2[C@H:17]([CH3:18])[C@H:16]3[N:13]([C:14](=[O:22])[C@@H:15]3[C@H:19]([OH:21])[CH3:20])[C:12]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH2:60][N:59]1[C:61]([O:63][C:64]([CH3:65])([CH3:66])[CH3:67])=[O:62])=[O:70]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 6342Acetonitrile2 回HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 15200286HCID 15200286、化合物HCID 594363011-(1,1-Dimethylethyl) (2S,4S)-4-(acetylthio)-1,2-pyrrolidinedicarboxylate

生成物 1

HCID 131730036HCID 131730036、化合物
収率 73.1%

反応条件

温度
0 °C

実験手順

A solution of 17.9 g (30 mmol) of p-nitrobenzyl(4R,5S,6S)-3-(diphenoxy-phosphoryloxy)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate in 150 ml of acetonitrile was added into a flask and the reaction mixture was cooled below −10° C. Then diisopropylethylamine (8 mL) and a solution of the intermediate (I-1) prepared by Intermediate Example 1 (10.1 g, 31 mmol) in 100 mL of acetonitrile were added and the reaction mixture was stirred at 0° C. for 15 hours. After the completion of the reaction, ethyl acetate (400 mL) was added to the reaction mixture for dilution and the mixture was washed successively with water and saturated brine. The organic layer was dried and concentrated to give 14.7 g (yield: 73.1%) of p-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-formyl[[furan-2-ylmethyl]amino]-1-(tert-butoxycarbonyl)pyrrolidine-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate, which is the intermediate II-1.

後処理

  1. temperaturethe reaction mixture was cooled below −10° C
  2. additionwere added
  3. additionwas added to the reaction mixture for dilution
  4. washthe mixture was washed successively with water and saturated brine
  5. customThe organic layer was dried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8e7a9f9c712f491ab400bbc044f953b8
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08293895B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート