Water → HCID 23144741, compound

HRID 1967754Notes

Reaction equation

HRID 1967754 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])=[N:5][C:4]=1[C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)=O.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:4]1[N:5]=[C:6]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])[S:7][C:3]=1[CH2:1][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 23144463HCID 23144463, compound

Product 1

HCID 23144741HCID 23144741, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Compound 85 (250 mg, 0.836 mmol) was dissolved in 1,2-dichloroethane (4 mL), and morpholine (0.15 mL, 1.67 mmol) and sodium triacetoxyborohydride (531 mg, 2.51 mmol) were 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 86 (302 mg, 98%).

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-8ec2c1bd9db44530ac0bc7421be8bc9a
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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