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Triethylamine → 2-{3-[2-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-ureido}-propionic Acid Methyl Ester

HRID 1012956
ノート
印刷プレビュー

反応式

HRID 1012956 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:15](=[O:22])[NH:14][N:13]=2)=[CH:7][C:3]=1C(O)=O.C([N:25]([CH2:28]C)CC)C.Cl.[CH3:31][O:32][C:33](=[O:37])[C@H:34]([CH3:36])[NH2:35].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:45])C=CC=CC=1>C(#N)C.CN1CCCC1=O>[CH3:31][O:32][C:33](=[O:37])[CH:34]([NH:35][C:28]([NH:25][C:3]1[CH:7]=[C:8]([CH2:11][C:12]2[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:15](=[O:22])[NH:14][N:13]=2)[CH:9]=[CH:10][C:2]=1[F:1])=[O:45])[CH3:36]
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

7

反応物 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2733257Alanine methyl ester hydrochlorideHCID 250050192-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-benzoic acid

生成物 1

HCID 577866402-{3-[2-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-ureido}-propionic Acid Methyl Ester

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
85 °C

実験手順

To a suspension of 2-fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)benzoic acid (11) (0.50 g, 1.650 mmol), in acetonitrile (2.5 ml) was added triethylamine (0.46 ml, 3.31 mmol) the suspension dissolved to afford a brown solution which was subsequently heated to 85° C. D/L alanine methyl ester hydrochloride (2.30 g, 1.650 mmol) dissolved in acetonitrile (5 ml) and N-methylpyrrolidinone (0.5 ml) was added simultaneously to the reaction mixture with diphenylphosphinic azide (0.357 ml, 1.650 mmol). After 40 minutes of heating the reaction mixture was cooled to ambient temperature and concentrated to vacuo. The crude oil was then subjected to flash chromatography, eluent hexane/ethyl acetate, 7:13 (Rf=0.14). Single peak in LC-MS, (0.67 g, 98% purity); m/z (LC-MS, ESP), RT=3.37 mins (M+H 403.2).

後処理

  1. dissolutiondissolved
  2. customto afford a brown solution which
  3. temperatureAfter 40 minutes of heating the reaction mixture
  4. temperaturewas cooled to ambient temperature
  5. concentrationconcentrated to vacuo

出典と根拠

ORDレコード
ord-f745de5a42854b289975365c67a7309a
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07981890B2

反応ノート

読み込み中…

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