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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
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HRID 1012956 반응식
[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]
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7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 13387N-methyl-2-pyrrolidone용매

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온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f745de5a42854b289975365c67a7309a
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07981890B2

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