Hydrochloric Acid → (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester

HRID 1058427ノート

反応式

HRID 1058427 の反応式
CN(C)C(N(C)C)=N.[CH3:9][O:10][C:11](=[O:40])[CH:12](P(OC)(OC)=O)[NH:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:17][C:16]=1Cl.[Br:41][C:42]1[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=1.[ClH:50]>O1CCCC1.O1CCOCC1>[CH3:9][O:10][C:11](=[O:40])/[C:12](/[NH:13][C:14](=[O:33])[C:15]1[CH:16]=[CH:17][C:18]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:19][C:20]=1[Cl:50])=[CH:46]/[C:45]1[CH:48]=[CH:49][C:42]([Br:41])=[CH:43][CH:44]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 664601,1,3,3-TetramethylguanidineHCID 707414-BromobenzaldehydeHCID 23560750HCID 23560750、化合物

生成物 1

HCID 59038409(Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester収率 62%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

実験手順

1,1,3,3-Tetramethylguanidine (0.047 g, 0.41 mmol) was added to a solution of rac.-N-[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 141; 0.10 g, 0.21 mmol) and 4-bromobenzaldehyde (0.076 g, 0.412 mmol) in tetrahydrofuran (1.5 mL). Dioxane (1.5 mL) was added to bring everything into solution and the reaction mixture was stirred at room temperature for 15 h. The solution was then poured into 1N hydrochloric acid solution and the aqueous phase was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residual material was chromatographed over silica gel (45% ethyl acetate/hexanes) to give (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester (69 mg, 62% yield).

後処理

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residual material was chromatographed over silica gel (45% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-8fa00c8d5dd44fd08da5f7d45474c37c
出典データセット
uspto-grants-2003_02
特許番号
US06515124B2

反応ノート

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