1,2-Dichloroethane → HCID 69655919, compound

HRID 857779Notes

Reaction equation

HRID 857779 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:16]1([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[CH2:31][NH2:32])[CH:20]=[N:19][N:18]=[N:17]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH:32][CH2:31][C:22]1[CH:23]=[C:24]([C:27]([F:28])([F:29])[F:30])[CH:25]=[CH:26][C:21]=1[N:16]1[CH:20]=[N:19][N:18]=[N:17]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 181649HOAtHCID 21866317HCID 21866317, compound

Product 1

HCID 69655919HCID 69655919, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(tert-butoxycarbonyl)-L-proline (39 mg, 0.18 mmol), 1-[2-(1H-tetraazol-1-yl)-5-(trifluoromethyl)phenyl]methanamine (42 mg, 0.17 mmol), EDC (49 mg, 0.26 mmol) and HOAt (12 mg, 0.09 mmol) in DMF (1 mL) was stirred at room temperature for 2 h. The crude product was purified by reverse phase HPLC followed by neutralization of an aqueous slurry of the compound with saturated aqueous K2CO3 and repeated extraction of the resulting aqueous mixture with EtOAc (the aqueous layer was saturated with NaCl before each extraction). The combined organic extracts were dried (anhydrous Na2SO4) and concentrated to afford the title compound as an oil which was carried on directly to the deprotection step (Step D below). LCMS (M+H): 441.2.

Workup

  1. customThe crude product was purified by reverse phase HPLC
  2. extractionextraction of the resulting aqueous mixture with EtOAc (the aqueous layer
  3. extractionwas saturated with NaCl before each extraction)
  4. dry with materialThe combined organic extracts were dried (anhydrous Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-854f6cbbb3d64cad86dc83e3a9d46acb
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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