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Hydrochloric Acid → (S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

HRID 2351086
ノート
印刷プレビュー

反応式

HRID 2351086 の反応式
[OH:1][C:2]1[C:3](=[O:18])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][NH:13][C:12]2=[O:17])=[O:9])[NH:6][CH:7]=1.CN([Si](C)(C)C)C(=O)C(F)(F)F.N1CCCNC1=O.[O:38]=[C:39]1[C@@H:42]([NH:43][C:44](=[O:53])[O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:41][NH:40]1.Cl[S:55]([N:58]=[C:59]=[O:60])(=[O:57])=[O:56].Cl>C(OCC)(=O)C.ClCCl>[OH:1][C:2]1[C:3](=[O:18])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:55]([NH:58][C:59]([N:40]3[CH2:41][C@H:42]([NH:43][C:44](=[O:53])[O:45][CH2:46][C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:39]3=[O:38])=[O:60])(=[O:57])=[O:56])[C:12]2=[O:17])=[O:9])[NH:6][CH:7]=1
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

9

反応物 6

HCID 313Hydrochloric AcidHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 70918Chlorosulfonyl isocyanateHCID 746152(1H)-Pyrimidinone, tetrahydro-2 回HCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 198480131,4-Dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide

生成物 1

HCID 86743424(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
0 °C

実験手順

2.73 g (10.82 mmol) 1,4-dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide and 8.63 g (43.29 mmol) N-methyl-N-trimethylsilyltrifluoroacetamide were dissolved in ethyl acetate and stirred for 1 hour (solution A). To a suspension of 2.38 g (10.82 mmol) (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 80 ml ethyl acetate was added 1.53 g (10.82 mmol) chlorosulfonyl isocyanate. After stirring for 1 hour, the solution was cooled to 0° C. and 9 ml dichloromethane and subsequently solution A were added. After stirring overnight at room temperature ice water was added and the pH was adjusted to 1.3 with 3N hydrochloric acid. The precipitate was filtered off, washed with water, dried in vacuo and slurried with ether. Yield 4.95 g, melting range 150°-230° C. (dec.).

後処理

  1. additionwas added
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-d6b1ec5eeed344889ebecb40d77e4209
出典データセット
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04871841

反応ノート

読み込み中…

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