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1-Hydroxybenzotriazole → (2R)-2-{o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzamido}-2-[p-(carboxy-methyl)phenyl]acetic acid

HRID 1289243
ノート
印刷プレビュー

反応式

HRID 1289243 の反応式
[NH2:1][C@H:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[F:28][C:29]1[CH:48]=[C:47]([N:49]([CH3:73])[CH:50]2[C:54]3[CH:55]=[C:56]4[C:61](=[CH:62][C:53]=3[CH2:52][CH2:51]2)[N:60]=[C:59]([CH3:63])[N:58]([CH2:64][O:65][C:66](=[O:71])[C:67]([CH3:70])([CH3:69])[CH3:68])[C:57]4=[O:72])[CH:46]=[CH:45][C:30]=1[C:31](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:32].ON1C2C=CC=CC=2N=N1>>[F:28][C:29]1[CH:48]=[C:47]([N:49]([CH3:73])[CH:50]2[C:54]3[CH:55]=[C:56]4[C:61](=[CH:62][C:53]=3[CH2:52][CH2:51]2)[N:60]=[C:59]([CH3:63])[N:58]([CH2:64][O:65][C:66](=[O:71])[C:67]([CH3:68])([CH3:69])[CH3:70])[C:57]4=[O:72])[CH:46]=[CH:45][C:30]=1[C:31]([NH:1][C@H:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4])=[O:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 11708267BistrimethylsilylacetamidHCID 19066320Pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoateHCID 54357908(R)-alpha-amino-p-carboxymethylphenylacetic acid

生成物 1

HCID 22885368
(2R)-2-{o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzamido}-2-[p-(carboxy-methyl)phenyl]acetic acid
収率 70.6%

実験手順

A solution of (R)-α-amino-p-carboxymethylphenylacetic acid (0.1 g, 0.48 mmol) and bis trimethylsilyl acetamide (0.195 g, 0.96 mmol in 5 ml of DMF) was stirred for 20 minutes at room temperature. To the solution was then added pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivalyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate (0.213 g, 0.4 mmol), prepared as described in Example 2, followed by N-hydroxybenzotriazole (10 mg) and the stirring was maintained for a further 5 hours. The reaction mixture was then evaporated to dryness and the crude material redissolved in ether. The ether layers were extracted with NaHCO3. The aqueous layers were acidified to pH 2.5 with 2N HCl and the precipiate was filtered off, washed with water and dried under vacuum to give (2R)-2-{o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzamido}-2-[p-(carboxy-methyl)phenyl]acetic acid (0.19 g), 85%) as a white solid;

後処理

  1. temperaturethe stirring was maintained for a further 5 hours
  2. customThe reaction mixture was then evaporated to dryness
  3. dissolutionthe crude material redissolved in ether
  4. extractionThe ether layers were extracted with NaHCO3
  5. filtrationthe precipiate was filtered off
  6. washwashed with water
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-b313fd722f8b4ee2acf741ab20e38f2c
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05747499

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート