Diisopropylethylamine → HCID 117607799、化合物

HRID 58800ノート

反応式

HRID 58800 の反応式
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.[C:34]([O:38][C:39]([NH:41][C@@H:42]([CH2:46][C:47]#[N:48])[C:43]([OH:45])=O)=[O:40])([CH3:37])([CH3:36])[CH3:35].[NH2:49][C@@H:50]([CH2:67][C:68]1[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][CH:69]=1)[C:51]([NH:53][C@@H:54]([CH2:61][C:62]1[CH2:66][CH2:65][CH2:64][CH:63]=1)[C:55]([C@@:57]1([CH3:60])[CH2:59][O:58]1)=[O:56])=[O:52]>CN(C=O)C.O.CCOC(C)=O>[C:47]([CH2:46][C@H:42]([NH:41][C:39](=[O:40])[O:38][C:34]([CH3:35])([CH3:36])[CH3:37])[C:43]([NH:49][C@@H:50]([CH2:67][C:68]1[CH:69]=[CH:70][C:71]([O:74][CH3:75])=[CH:72][CH:73]=1)[C:51]([NH:53][C@@H:54]([CH2:61][C:62]1[CH2:66][CH2:65][CH2:64][CH:63]=1)[C:55]([C@@:57]1([CH3:60])[CH2:59][O:58]1)=[O:56])=[O:52])=[O:45])#[N:48]

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 7019873Boc-beta-cyano-L-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117607712HCID 117607712、化合物

生成物 1

HCID 117607799HCID 117607799、化合物収率 45%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sequentially HATU (1.21 g, 3.20 mmol) and DIEA (1.35 mL, 7.8 mmol) were added to a 0° C. solution of (S)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid and (S)-2-amino-N-((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)-3-(4-methoxyphenyl)propanamide (TFA salt, 2.1 mmol) in DMF (20 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 3 h. EtOAc (100 mL) and water (100 mL) was added. The aqueous layer was extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (200 mL×3), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:2) to afford tert-butyl ((S)-3-cyano-1-(((S)-1-(((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyl oxiran-2-yl)-1-oxopropan-2-yl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)carbamate (590 mg, 45% yield).

後処理

  1. extractionThe aqueous layer was extracted with EtOAc (50 mL×3)
  2. washThe combined organic phases were washed with brine (200 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:2)

出典と根拠

ORDレコード
ord-9f08416fb76e4709bb36815cde0aee42
出典データセット
uspto-grants-2016_09
特許番号
US09434761B2

反応ノート

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