Water → HCID 59468924, compound

HRID 1690088Notes

Reaction equation

HRID 1690088 reaction equation
[NH2:1][C:2]([C@:4]1([CH3:23])[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:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[C:27]#[N:28].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]([C@:4]1([CH3:23])[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:25]3[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=3[C:27]#[N:28])=[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 59468953HCID 59468953, compound

Product 1

HCID 59468924HCID 59468924, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-hydroxyphenyl)-2-methyl-1-pyrrolidinecarboxylate (D10, 60 mg, 0.187 mmol), 2-fluorobenzonitrile (45 mg, 0.374 mmol) and potassium carbonate (39 mg, 0.280 mmol) in DMF (2 ml) was heated under microwave irradiation for 30 min to 120° C. Water and ethyl acetate were added to the mixture, and the organic layer was washed with ice cold water. The solution was dried (Na2SO4) and evaporated. The crude material was purified by chromatography on silica gel using cyclohexane/ethyl acetate (7:3 to 6:4) to afford the title compound (78 mg); Rt (HPLC): 5.44 min; R (cyclohexane:ethyl acetate=1:1): 0.21; MS: (ES/+) m/z: 444 [M+Na+]; C24H27N3O4 requires 421.

Workup

  1. washthe organic layer was washed with ice cold water
  2. dry with materialThe solution was dried (Na2SO4)
  3. customevaporated
  4. customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-960853f0bedd402cba741e46bc7a24e1
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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