Acetic Acid → HCID 66652745, compound

HRID 572573Notes

Reaction equation

HRID 572573 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)=O.[C:14]([O:18][C:19](=[O:22])[CH2:20][NH2:21])([CH3:17])([CH3:16])[CH3:15].[C:23]([BH3-])#N.[Na+].C(O)(=O)C.C=O>C(Cl)Cl.CO.C(Cl)Cl.O>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([CH:4]([N:21]([CH3:23])[CH2:20][C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:22])[CH2:3][O:2][CH3:1])=[CH:7][CH:8]=1)#[N:11]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 151417Glycine tert-butyl esterHCID 318403HCID 318403, compoundHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 66652745HCID 66652745, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 4-(2-methoxyacetoyl)benzonitrile (0.338 g; 1.93 mmol) and glycine tert-butyl ester (0.382 mg; 2.90 mmol) in DCM/MeOH (1:1; 10 mL) was stirred at ambient temperature for 1 hour. Sodium cyanoborohydride (0.182 g; 2.90 mmol) and acetic acid (0.166 mL; 2.90 mmol) were added to the reaction mixture and the mixture stirred for 18 hours. Aqueous paraformaldehyde (0.787 mL) and sodium cyanoborohydride (0.182 g; 2.90 mmol) were added and the reaction mixture stirred for a further 72 hours. The reaction mixture was diluted with DCM and water and then poured through a hydrophobic frit. The filtrate was evaporated in vacuo. The residue was purified by flash chromatography eluting with iso-hexane/EtOAc (3:2) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.62-7.61 (m, 2H), 7.51-7.49 (m, 2H), 4.09-4.06 (m, 1H), 3.62 (m, 2H), 3.42-3.37 (m, 1H), 3.29 (s, 3H), 3.21-3.17 (m, 1H), 2.39 (s, 3H), 1.47 (s, 9H).

Workup

  1. stirringthe reaction mixture stirred for a further 72 hours
  2. additionpoured through a hydrophobic frit
  3. customThe filtrate was evaporated in vacuo
  4. customThe residue was purified by flash chromatography
  5. washeluting with iso-hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-85b55804e9c4469a9444a08aa7f68abc
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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