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Diisopropylethylamine → 4-{2-[2-(Benzyloxycarbonyl-methyl-amino)-propionylamino]-3-tert-butoxy-butyryl}-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

HRID 1949630
ノート
印刷プレビュー

反応式

HRID 1949630 の反応式
[C:1]([N:11]([CH3:17])[C@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:51]([O:58][C:59]([N:61]1[CH2:65][CH:64]([C:66]2[C:74]3[C:69](=[CH:70][C:71]([F:75])=[CH:72][CH:73]=3)[NH:68][CH:67]=2)[CH:63]2[N:76]([C:79](=[O:89])[CH:80]([NH2:88])[CH:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])[CH3:82])[CH2:77][CH2:78][CH:62]12)=[O:60])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>CN1C(=O)CCC1.CCOC(C)=O>[CH2:51]([O:58][C:59]([N:61]1[CH2:65][CH:64]([C:66]2[C:74]3[C:69](=[CH:70][C:71]([F:75])=[CH:72][CH:73]=3)[NH:68][CH:67]=2)[CH:63]2[N:76]([C:79](=[O:89])[CH:80]([NH:88][C:14](=[O:16])[CH:12]([N:11]([C:1]([O:3][CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:2])[CH3:17])[CH3:13])[CH:81]([O:83][C:84]([CH3:86])([CH3:85])[CH3:87])[CH3:82])[CH2:77][CH2:78][CH:62]12)=[O:60])[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=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

7

反応物 4

HCID 81531DiisopropylethylamineHCID 7016365Z-N-Me-Ala-OHHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 674088224-(2-Amino-3-tert-butoxy-butyryl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

生成物 1

HCID 67409178
4-{2-[2-(Benzyloxycarbonyl-methyl-amino)-propionylamino]-3-tert-butoxy-butyryl}-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution containing Cbz-N(Me)Ala-OH (119 mg, 0.5 mmol) in anhydrous NMP (4 mL) was cooled to 0° C. HATU (189 mg, 0.5 mmol) and DIPEA (111 mg, 0.8 mmol) were added followed by the addition of crude 44 (280 mg, 0.5 mmol) in anhydrous NMP (4 mL). The reaction mixture was slowly warmed to ambient temperature. After 2 h, the reaction mixture was diluted with EtOAc and washed successively with 1M HCl, aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 330 mg of crude 45 as an amber-colored oil which was used without further purification. Mass spectrum, m/z [756.4] (M+H)+.

後処理

  1. temperatureThe reaction mixture was slowly warmed to ambient temperature
  2. washwashed successively with 1M HCl, aqueous NaHCO3, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8f0acc856d804a70b0d6fa62d8e0cb8d
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08399683B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート