Cyclobutylamine → HCID 66857076, compound

HRID 1970643Notes

Reaction equation

HRID 1970643 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1[CH:22]=NC2N(O)N=[N:25][C:19]=2[CH:18]=1.C1(N)CCC1.C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)CCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:16])[NH:25][CH:19]1[CH2:18][CH2:17][CH2:22]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 75645CyclobutylamineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 181649HOAtHCID 516892Sodium Bicarbonate

Product 1

HCID 66857076HCID 66857076, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.00 g (2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester in 20 ml DMF were added 1.18 g HOAT, 615 mg cyclobutylamine and 1.66 g EDC. After stirring for 12 h saturated NaHCO3 solution (3 ml) was added and the mixture passed through a Chem Elute® cartridge eluting with DCM. The crude product obtained after evaporation of the solvent was purified by filtering over a short plug of silica eluting with ethyl acetate. Yield: 1.22 g

Workup

  1. additionwas added
  2. washElute® cartridge
  3. washeluting with DCM

Sources & evidence

ORD record
ord-0ac5799e84bd47729d4211d486e5efd4
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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