Potassium Carbonate → HCID 86760632, compound

HRID 1393643Notes

Reaction equation

HRID 1393643 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]([NH:8][CH2:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]#[N:18])=[O:11])([CH3:7])[CH3:6].[CH:19](OC1C=CC([N+]([O-])=O)=CC=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:17]([C@@H:13]1[CH2:14][CH2:15][CH2:16][N:12]1[C:10](=[O:11])[CH2:9][NH:8][C:5]([CH3:7])([CH3:6])[CH2:4][NH:3][CH:19]=[O:20])#[N:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 746284-Nitrophenyl formateHCID 57500553HCID 57500553, compound

Product 1

HCID 86760632HCID 86760632, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-1-[(2-Amino-1,1-dimethylethyl)aminoacetyl]-pyrrolidine-2-carbonitrile dihydrochloride (1.48 g) was dissolved in acetonitrile (50 ml), and 4-nitrophenyl formate (1.00 g) and potassium carbonate (1.37 g) were added thereto and stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 5:1) to give (S)-N-{2-[2-(2-cyanopyrrolidin-1-yl)-2-oxoethylamino]-2-methyl-1-propyl}-formamide (693 mg, Y.:55%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 5:1)

Sources & evidence

ORD record
ord-5b8d15268cd54e2f84a9eab581cd2afd
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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