Water → (4-{4-(2-Azidoacetyl)-phenyl]-cyclohexyl}-acetic acid ethyl ester

HRID 76034Notes

Reaction equation

HRID 76034 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19]Br)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].[N-:23]=[N+:24]=[N-:25].[Na+].O.CCOC(C)=O>CC(C)=O.O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][N:23]=[N+:24]=[N-:25])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86634685HCID 86634685, compound

Product 1

HCID 86634688(4-{4-(2-Azidoacetyl)-phenyl]-cyclohexyl}-acetic acid ethyl esterYield 103.7%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of {4-[4-(2-bromoacetyl)-phenyl]-cyclohexyl}-acetic acid ethyl ester (166 mg, 0.451 mmol) in acetone/water (4:1, v/v, 5 mL) is added NaN3 (44 mg, 0.676 mmol) and the mixture is stirred at ambient temperature for 2 h. Water (10 mL) is added and EtOAc is used to extract. The organic phase is dried with MgSO4, concentrated, and dried under high vacuum to give the title compound (154 mg): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.05-1.16 (m, 2H) 1.20 (t, J=7.07 Hz, 3H) 1.40-1.49 (m, 2H) 1.84 (d, J=10.11 Hz, 4H) 1.76-1.87 (m, 1H) 2.17 (d, J=6.82 Hz, 2H) 2.48 (tt, J=112.25, 3.03 Hz, 1H) 4.08 (q, J=7.16 Hz, 2H) 4.45 (s, 2H) 7.25 (d, J=8.34 Hz, 2H) 7.76 (d, J=8.34 Hz, 2H).

Workup

  1. extractionto extract
  2. dry with materialThe organic phase is dried with MgSO4
  3. concentrationconcentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-06cbf17ed72b48ca8772d518788aedd3
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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