Sodium Bicarbonate → HCID 71268277, compound

HRID 1519677Notes

Reaction equation

HRID 1519677 reaction equation
Cl.[O:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]2[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[O:2]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][C:11]2[CH:12]=[CH:13][C:14]([C:17]#[C:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:28][CH:29]=3)=[CH:15][CH:16]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 230902141,4-Oxazepane hydrochlorideHCID 86679257HCID 86679257, compound

Product 1

HCID 71268277HCID 71268277, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

1,4-Oxazepane hydrochloride (1.6 g) and acetic acid (0.90 mL) were added to a chloroform (20 mL) solution of ethyl 4-[(4-formylphenyl)ethynyl]benzoate (2.1 g) as obtained in Example 5-(1), and the mixture was stirred for 3.5 hours at room temperature, and then for 2 hours at 60° C. Then, sodium triacetoxyborohydride (2.7 g) was added, and the mixture was stirred for 16 hours at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (gradient elution with chloroform/methanol=100/0→93/7) to obtain ethyl 4-{[4-(1,4-oxazepan-4-ylmethyl)phenyl]ethynyl}benzoate (yellow solid) (1.5 g, 52%).

Workup

  1. customas obtained in Example 5-(1)
  2. waitfor 2 hours at 60° C
  3. stirringthe mixture was stirred for 16 hours at room temperature
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThen, the desiccant was filtered out
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by OH type silica gel chromatography (gradient elution with chloroform/methanol=100/0→93/7)

Sources & evidence

ORD record
ord-4f1bcef28da247e2af029ca8060efda5
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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