Formaldehyde → HCID 67351671, compound

HRID 1672841Notes

Reaction equation

HRID 1672841 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:19]=3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:31]=1)[CH3:2].C=O.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH:25]4[CH2:30][CH2:29][N:28]([CH3:34])[CH2:27][CH2:26]4)[CH:19]=3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:31]=1)[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67351083HCID 67351083, compound

Product 1

HCID 67351671HCID 67351671, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Compound 147 (100 mg, 0.237 mmol) obtained in Example 147 was dissolved in 1,2-dichloroethane (5 mL), and the mixture was stirred at room temperature for 2 hours after adding 37% formalin solution (0.0530 mL, 0.710 mmol) and sodium triacetoxyborohydride (150 mg, 0.710 mmol). Thereafter, a saturated aqueous sodium bicarbonate solution was added to the mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and crystallized from diethyl ether to give the title compound (Compound 148) (93.9 mg, 91%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-237fbd2b3acb4785a56601dea98db9fc
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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