Water → HCID 59596693, compound

HRID 2264803Notes

Reaction equation

HRID 2264803 reaction equation
[NH2:1][C:2]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[N:5]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:3].F[C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[C:26]#[N:27].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:24]3[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=3[C:26]#[N:27])=[CH:11][CH:10]=2)[N:5]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 678552-FluorobenzonitrileHCID 59164822HCID 59164822, compound

Product 1

HCID 59596693HCID 59596693, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-hydroxyphenyl)-1-pyrrolidinecarboxylate (D13, 50 mg, 0.163 mmol), 2-fluorobenzonitrile (40 mg, 0.326 mmol) and K2CO3 (34 mg, 0.245 mmol) in DMF (1 ml) was heated under microwave irradiation for 30 min at 120° C. Then water and ethyl acetate were added to the mixture. The organic layer was washed with ice cold brine. The solution was dried over Na2SO4 and the solvent removed under reduced pressure. The crude material was purified by chromatography on silica gel using cyclohexanes/ethyl acetate (75:25) to afford the title compound (50 mg, 75%); Rf (cyclohexanes:ethyl acetate=1:1): 0.10; Rt (HPLC) 5.17 min.; MS: (ES/+) m/z: 430 [M+Na+], C23H25N3O4 requires 407.

Workup

  1. washThe organic layer was washed with ice cold brine
  2. dry with materialThe solution was dried over Na2SO4
  3. customthe solvent removed under reduced pressure
  4. customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a7f17b1594b64fcf9c5642ad51d83e56
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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