Acetic Acid → n-((1s,2r)-1-((4-Chlorophenyl)methyl)-3-(((4's)-6'-(2,2-dimethylbutyl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridin]-4'-yl)amino)-2-hydroxypropyl)acetamide

HRID 1009133ノート

反応式

HRID 1009133 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:33][C:34](=[O:36])[CH3:35])[C@H:10]([OH:32])[CH2:11][NH:12][C@@H:13]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([CH2:23][C:24]([CH3:28])([CH3:27])[C:25]#[CH:26])[CH:21]=3)[O:16][C:15]3([CH2:31][CH2:30][CH2:29]3)[CH2:14]2)=[CH:4][CH:3]=1.CC(O)=O>CO.C(O)(N=NC(O)=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:33][C:34](=[O:36])[CH3:35])[C@H:10]([OH:32])[CH2:11][NH:12][C@@H:13]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([CH2:23][C:24]([CH3:27])([CH3:28])[CH2:25][CH3:26])[CH:21]=3)[O:16][C:15]3([CH2:31][CH2:30][CH2:29]3)[CH2:14]2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 176Acetic Acid2 回HCID 87349212n-((1s,2r)-1-((4-Chlorophenyl)methyl)-3-(((4's)-6'-(2,2-dimethyl-3-butyn-1-yl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridin]-4'-yl)amino)-2-hydroxypropyl)acetamide

生成物 1

HCID 67305464n-((1s,2r)-1-((4-Chlorophenyl)methyl)-3-(((4's)-6'-(2,2-dimethylbutyl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridin]-4'-yl)amino)-2-hydroxypropyl)acetamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 415805Diazenedicarboxylic acid溶媒

実験手順

The compound of Example 492 (0.100 g, 0.196 mmol) was dissolved in MeOH (2 mL) and diazenedicarboxylic acid, dipotassium salt (0.762 g, 3.92 mmol) was added. HOAc (0.673 ml, 11.8 mmol) in MeOH (2 mL) was slowly added to the heterogeneous solution and the reaction was stirred. After all the acetic acid was added and the solution went from yellow to clear and upon complete reduction, the reaction was concentrated and partitioned between 1 N NaOH and DCM. The aqueous was layer was extracted with DCM and the combined organics were washed with brine and concentrated. The crude material was dissolved in a minimal amount of MeOH and directly purified by reverse phase HPLC to afford the title compound. MS m/z: 514.2 (M+1).

後処理

  1. concentrationthe reaction was concentrated
  2. custompartitioned between 1 N NaOH and DCM
  3. extractionwas extracted with DCM
  4. washthe combined organics were washed with brine
  5. concentrationconcentrated
  6. dissolutionThe crude material was dissolved in a minimal amount of MeOH
  7. customdirectly purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-1721051cec2d46d08fa6977576cf239e
出典データセット
uspto-grants-2011_07
特許番号
US07973047B2

反応ノート

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