Water → HCID 23144685, compound

HRID 1361778Notes

Reaction equation

HRID 1361778 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([CH:19]=O)=[C:12]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([CH2:19][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[C:12]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 23144187HCID 23144187, compound

Product 1

HCID 23144685HCID 23144685, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Compound 92 (1.58 g, 5.37 mmol) and morpholine (0.64 mL, 10.7 mmol) were dissolved in 1,2-dichloroethane (26 mL), and sodium triacetoxyborohydride (3.41 g, 16.1 mmol) was added thereto, followed by stirring overnight at room temperature. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=30:1) to afford the entitled Compound 93 (1.15 g, 57%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-1480064818904cd0ad3bc8aafc707e74
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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