Potassium Carbonate → HCID 66724763, compound

HRID 1799217Notes

Reaction equation

HRID 1799217 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11](C(OC(C)(C)C)=O)[C:10](=[O:20])[CH2:9]2)=[CH:4][C:3]=1[OH:21].C([O-])([O-])=[O:23].[K+].[K+].Br.Br[CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C(O)C>[ClH:1].[NH2:11][CH2:12][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:21][CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[CH:4]=1)[CH2:9][C:10]([OH:20])=[O:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127522194-(Bromomethyl)pyridine hbrHCID 86646671HCID 86646671, compound

Product 1

HCID 66724763HCID 66724763, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl (4R)-4-(4-chloro-3-hydroxyphenyl)-2-oxopyrrolidinecarboxylate (68a) (1.0 equiv.) in ethanol (0.4M) was added K2CO3 (2 equiv.) followed by an appropriate electrophile (1.5 equiv., e.g. 4-bromomethylpyridine hydrobromide). The reaction mixture was heated overnight at 90° C. The mixture was cooled to room temperature and the solvent removed. The crude residue was treated with a 6N HCl aqueous solution (0.1M) and heated for 3 h at 90° C. The title compound (68) was obtained following purification by HPLC purification. 1H-NMR (400 MHz, CD3OD): δ 2.60-2.66 (dd, J=16.4, 7.6 Hz, 1H), 2.74-2.78 (dd, J=16.4, 7.2 Hz, 1H), 3.17-3.24 (m, 1H), 5.28 (s, 2H), 8.53-8.54 (d, J=4.0 Hz, 1H), 7.56-7.57 (d, J=4 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.09-7.09 (d, J=2.0 Hz, 1H), 6.92-6.95 (d, J=4.0 Hz, 1H); MS (ESI) m/z 321.01 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent removed
  3. additionThe crude residue was treated with a 6N HCl aqueous solution (0.1M)
  4. temperatureheated for 3 h at 90° C

Sources & evidence

ORD record
ord-a62940b29a8b4ab5b9760cb7e5d224af
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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