Acetic Acid → HCID 59655723, compound

HRID 2054400Notes

Reaction equation

HRID 2054400 reaction equation
[CH3:1][NH:2][CH3:3].C1COCC1.[CH:9]([N:22]1[CH2:25][C:24](=O)[CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C.[C-:31]#[N:32].[K+]>CO>[CH:9]([N:22]1[CH2:25][C:24]([N:2]([CH3:3])[CH3:1])([C:31]#[N:32])[CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 674DimethylamineHCID 8028TetrahydrofuranHCID 9032Potassium CyanideHCID 37355581-(Diphenylmethyl)azetidin-3-one

Product 1

HCID 59655723HCID 59655723, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2M dimethylamine in THF (3.92 ml, 7.83 mmol) was added to 1-benzhydrylazetidin-3-one (1.43 g, 6.03 mmol). After stirring 5 minutes, acetic acid (0.450 ml, 7.83 mmol), solid KCN (0.510 g, 7.83 mmol), and methanol (0.5 ml) were added at room temperature. After stirring for 5 minutes, the mixture was heated to 60° C. for 19 hours. The reaction was cooled and extracted from saturated aqueous NaHCO3 with ethyl acetate. The combined extracts were dried (Na2SO4), and concentrated, in vacuo, to afford I-3A-3a as a foam (1.77 g, quantitative): +ESI MS (M+1) 292.3; 1H NMR (400 MHz, CD2Cl2) δ 7.44 (d, J=7.5 Hz, 4H), 7.29 (t, J=7.5 Hz, 4H), 7.21 (t, J=7.3 Hz, 2H), 4.41 (s, 1H), 3.58 (d, J=8.3 Hz, 2H), 3.05 (d, J=8.3 Hz, 2H), 2.13 (s, 6H).

Workup

  1. stirringAfter stirring for 5 minutes
  2. temperatureThe reaction was cooled
  3. extractionextracted from saturated aqueous NaHCO3 with ethyl acetate
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated, in vacuo
  6. customto afford I-3A-3a as a foam (1.77 g, quantitative)

Sources & evidence

ORD record
ord-0920082425b7465484472568ab4f880e
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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