Cyclobutylamine → HCID 66857076, compound

HRID 467521Notes

Reaction equation

HRID 467521 reaction equation
C1C=NC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[CH:23]1([NH2:27])[CH2:26][CH2:25][CH2:24]1.[C:28]([O:32][C:33]([N:35]1[CH2:42][C@H:41]([OH:43])[CH2:40][C@H:36]1[C:37](O)=[O:38])=[O:34])([CH3:31])([CH3:30])[CH3:29].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH:23]1([NH:27][C:37]([C@@H:36]2[CH2:40][C@@H:41]([OH:43])[CH2:42][N:35]2[C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])=[O:38])[CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 5

HCID 75645CyclobutylamineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66857076HCID 66857076, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.17 g of HOAT, 1.60 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.615 g of cyclobutylamine are added to a solution of 2.0 g of (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline in 20 ml of DMF. 1.5 ml of a saturated solution of NaHCO3 is added and the reaction mixture is filtered on a Chem Elut® cartridge, eluting with DCM. The solvents are concentrated under vacuum and the residue is purified by filtration on silica gel, eluting with EtOAc. 1.22 g of the expected compound is obtained.

Workup

  1. filtrationthe reaction mixture is filtered on a Chem Elut® cartridge
  2. washeluting with DCM
  3. concentrationThe solvents are concentrated under vacuum
  4. filtrationthe residue is purified by filtration on silica gel
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-9bf5c4761b224bc381b6136f6ac08fa4
Source dataset
uspto-grants-2014_01
Patent number
US08623862B2

Reaction notes

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