1,2-Dichloroethane → HCID 69939709, compound

HRID 1058241Notes

Reaction equation

HRID 1058241 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:14][N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)=[C:10]([CH:13]=1)[CH2:11][NH2:12].[C:21]([N:28]1[CH2:35][CH2:34][CH2:33][C@H:29]1[C:30](O)=[O:31])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:14][N:15]2[CH2:16][C:17]([F:20])([F:19])[CH2:18]2)=[C:10]([CH:13]=1)[CH2:11][NH:12][C:30](=[O:31])[C@@H:29]1[CH2:33][CH2:34][CH2:35][N:28]1[C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 181649HOAtHCID 18672412HCID 18672412, compound

Product 1

HCID 69939709HCID 69939709, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (80.2 mg, 0.42 mmol) was added to a stirred mixture of 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzylamine (68.8 mg, 0.28 mmol), N-BOC-L-proline (60.0 mg, 0.28 mmol) and HOAT (19.0 mg, 0.14 mmol) in DMF (2.5 mL). After 66 h the reaction mixture was concentrated and the residue was partitioned between EtOAc and 10% NaHCO3. The organic layer was washed with water and brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography on silica (eluting with EtOAc/CHCl3, 1:5) to give N-{5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzyl}-1-(tert-butoxycarbonyl)-L-prolinamide (64.2 mg) as a glass: MS: 444.4 (M+1).

Workup

  1. concentrationAfter 66 h the reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and 10% NaHCO3
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by chromatography on silica (eluting with EtOAc/CHCl3, 1:5)

Sources & evidence

ORD record
ord-0e6e98e9474946f0b9f3dfb6f726f0dc
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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