Hydrochloric Acid → 4-((4-((((3-Isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl)amino)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-carboxylic acid

HRID 16581

反応式

HRID 16581 の反応式
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3([C:30]([O:32]C(C)(C)C)=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH2:19][CH2:18]2)=[O:14])[C:5]1=[O:37])([CH3:3])[CH3:2].Cl>C1COCC1>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH:15][CH2:16][CH:17]2[CH2:18][CH2:19][N:20]([CH2:23][C:24]3([C:30]([OH:32])=[O:31])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH2:21][CH2:22]2)=[O:14])[C:5]1=[O:37])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 68584353tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

生成物 1

HCID 117122634-((4-((((3-Isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl)amino)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-carboxylic acid収率 92.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (3.67 g, 7.13 mmol, step 6) in THF (80 mL) was added conc. HCl (40 mL) at 0° C. and the resulting mixture was stirred for 20 h at room temperature. The mixture was concentrated to remove the solvent and the residue was poured into sat. NaHCO3 aq. The mixture was extracted with CH2Cl2 for three times and the organic layer was dried over Na2SO4. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting MeOH/CH2Cl2 (1:10) to give 3.01 g (92%) of the title compound. The product was recrystalized from THF to give the titled compound (0.893 g) as white crystals.

後処理

  1. concentrationThe mixture was concentrated
  2. customto remove the solvent
  3. additionthe residue was poured into sat. NaHCO3 aq. The mixture
  4. extractionwas extracted with CH2Cl2 for three times
  5. dry with materialthe organic layer was dried over Na2SO4
  6. customRemoval of the solvent
  7. customgave a residue, which
  8. customwas chromatographed on a column of silica gel
  9. washeluting MeOH/CH2Cl2 (1:10)

出典と根拠

ORDレコード
ord-9f999b3030c14b709d54604a86c703ac
出典データセット
uspto-grants-2010_06
特許番号
US07737163B2

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