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4-Methylmorpholine → 3-[(N-Boc-Piperidin-4-ylmethyl)aminocarbonyl]benzoyl-2(S)-3-pyridylsulfonylamino-beta-alanyl-glycine benzyl ester

HRID 265905
ノート
印刷プレビュー

反応式

HRID 265905 の反応式
CO[C:3](=[O:42])[C@@H:4]([NH:32][S:33]([C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)(=[O:35])=[O:34])[CH2:5][NH:6][C:7](=[O:31])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)=[O:15])[CH:9]=1.O[Li].O.[CH2:46]([O:53][C:54](=[O:57])[CH2:55][NH2:56])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.Cl.CN1CCOCC1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C.C1COCC1.CO.O>[CH2:46]([O:53][C:54](=[O:57])[CH2:55][NH:56][C:3](=[O:42])[C@@H:4]([NH:32][S:33]([C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)(=[O:34])=[O:35])[CH2:5][NH:6][C:7](=[O:31])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:19]2)=[O:15])[CH:9]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 168937Lithium hydroxide, monohydrateHCID 11701227Benzyl 2-aminoacetate hydrochlorideHCID 867510973-[(N-Boc-Piperidin-4-ylmethyl)aminocarbonyl]benzoyl-2(S)-3-pyridylsulfonylamino-beta-alanine methyl ester

生成物 1

HCID 86751096
3-[(N-Boc-Piperidin-4-ylmethyl)aminocarbonyl]benzoyl-2(S)-3-pyridylsulfonylamino-beta-alanyl-glycine benzyl ester

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

A solution of 31-1 (0.75 g, 1.5 mmol) in 1:1:1 THF/MeOH/H2O (15 mL) was treated with LiOH·H2O (0.37 g, 8.8 mmol). After 45 min. the solution was concentrated, diluted with water, washed with EtOAc. The aqueous layer was acidified to pH 2-3 with 10% KHSO4 and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and evaporated to give an acid which was dissolved in acetonitrile (3 mL) and treated with glycine benzyl ester·HCl (0.1 g, 0.5 mmol), N-methylmorpholine (0.11 mL, 0.98 mmol), and BOP reagent (0.26 g, 0.58 mmol) for 24 h. The solution was concentrated, dissolved in water and EtOAc and the layers separated. The organic layer was dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, 70% acetone/hexanes) gave 31-2 as a white solid.

後処理

  1. concentrationAfter 45 min. the solution was concentrated
  2. additiondiluted with water
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give an acid which
  9. concentrationThe solution was concentrated
  10. dissolutiondissolved in water
  11. customEtOAc and the layers separated
  12. dry with materialThe organic layer was dried (Na2SO4)
  13. filtrationfiltered
  14. customevaporated

出典と根拠

ORDレコード
ord-7e9ed2f007cb48f0bc00c794dc4226d5
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05648368

反応ノート

読み込み中…

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