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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
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HRID 265905 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7e9ed2f007cb48f0bc00c794dc4226d5
출처 데이터셋
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05648368

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