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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (1s,3s)-1-((1S)-1-{[(2,6-dimethylphenoxy)acetyl]amino}-2-phenylethyl)-3-{[(2s)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanoyl]amino}-4-phenylbutyl 4-{[bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoate

HRID 2238325
ノート
印刷プレビュー

反応式

HRID 2238325 の反応式
[CH2:1]([C@H:8]([NH:33][C:34](=[O:46])[C@@H:35]([N:39]1[CH2:44][CH2:43][CH2:42][NH:41][C:40]1=[O:45])[CH:36]([CH3:38])[CH3:37])[CH2:9][C@H:10]([OH:32])[C@@H:11]([NH:19][C:20](=[O:31])[CH2:21][O:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:47]([O:54][P:55]([O:65][CH2:66][C:67]([CH3:73])([CH3:72])[CH2:68][C:69](O)=[O:70])([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH2:58]([O:57][P:55]([O:65][CH2:66][C:67]([CH3:73])([CH3:72])[CH2:68][C:69]([O:32][C@H:10]([C@@H:11]([NH:19][C:20](=[O:31])[CH2:21][O:22][C:23]1[C:24]([CH3:30])=[CH:25][CH:26]=[CH:27][C:28]=1[CH3:29])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:9][C@@H:8]([NH:33][C:34](=[O:46])[C@@H:35]([N:39]1[CH2:44][CH2:43][CH2:42][NH:41][C:40]1=[O:45])[CH:36]([CH3:38])[CH3:37])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:70])([O:54][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:56])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2 回HCID 92727LopinavirHCID 540936554-{[Bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoic acid2 回

生成物 1

HCID 87319122(1s,3s)-1-((1S)-1-{[(2,6-dimethylphenoxy)acetyl]amino}-2-phenylethyl)-3-{[(2s)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanoyl]amino}-4-phenylbutyl 4-{[bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoate
収率 84%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution containing the compound of Example 3 (0.075 g, 0.12 mmol), the product from Example 9C (0.056 g), and DMAP (0.017 g) in DMF (1.2 mL) was added EDAC (0.027 g) and the mixture was stirred at room temperature for 16 hours. Additional product from Example 9C (0.056 g) and EDAC (0.027 g) were added and the reaction was stirred at room temperature for 3 hours. The solvent was evaporated and the reaction mixture was partitioned between ethyl acetate and aqueous NaHCO3. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with a gradient starting with 33% ethyl acetate in chloroform and ending with 5% methanol in chloroform, to give the title compound (0.101 g, 84%).

後処理

  1. stirringthe reaction was stirred at room temperature for 3 hours
  2. customThe solvent was evaporated
  3. customthe reaction mixture was partitioned between ethyl acetate and aqueous NaHCO3
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with a gradient

出典と根拠

ORDレコード
ord-8dad767f10804227b607a0aefad3f37b
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07718633B2

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