Acetic Acid → Tert-butyl 2-(1-(4-cyanophenyl)-2-hydroxyethylamino)acetate

HRID 572576Notes

Reaction equation

HRID 572576 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.[C:13]([O:17][C:18](=[O:21])[CH2:19][NH2:20])([CH3:16])([CH3:15])[CH3:14].C([BH3-])#N.[Na+].C(O)(=O)C>C(Cl)Cl.CO.C(Cl)Cl.O>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([CH:3]([NH:20][CH2:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:21])[CH2:2][OH:1])=[CH:6][CH:7]=1)#[N:10]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 151417Glycine tert-butyl esterHCID 5003444Sodium cyanoborohydrideHCID 179928864-(2-Hydroxyacetyl)benzonitrile

Product 1

HCID 66652797Tert-butyl 2-(1-(4-cyanophenyl)-2-hydroxyethylamino)acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 4-(2-hydroxyacetoyl)benzonitrile (0.730 g; 4.53 mmol) and glycine tert-butyl ester (0.896 mg; 6.80 mmol) in DCM/MeOH (1:1; 12 mL) was stirred at ambient temperature for 1 hour. Sodium cyanoborohydride (0.342 g; 6.80 mmol) and acetic acid (0.389 mL; 6.80 mmol) were added to the reaction mixture and the mixture stirred for 18 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 7.65 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 3.88-3.85 (m, 1H), 3.76-3.72 (m, 1H), 3.59-3.55 (m, 1H), 3.32 (d, J=17.6 Hz, 1H), 3.15 (d, J=17.6 Hz, 1H), 1.49 (s, 9H).

Workup

  1. additionpoured through a hydrophobic frit
  2. customThe filtrate was evaporated in vacuo
  3. customThe residue was purified by flash chromatography
  4. washeluting with iso-hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-ed9c8940ec234398bef767eb43eb62d0
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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