1,2-Dichloroethane → HCID 58760139, compound

HRID 857758Notes

Reaction equation

HRID 857758 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]2[CH:21]=[N:20][N:19]=[N:18]2)=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1.[CH:22]1[CH:27]=[C:26]2N=NN(O)[C:25]2=[CH:24][CH:23]=1.[OH2:32].[CH2:33](Cl)[CH2:34]Cl.C(N(C(C)C)CC)(C)C.CN(C=[O:50])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]2[CH:21]=[N:20][N:19]=[N:18]2)=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:33](=[O:50])[C@H:34]([OH:32])[C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:27]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 69655818N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

Product 1

HCID 58760139HCID 58760139, compound

Procedure

To a solution of R-mandelic acid (60 mg, 0.39 mmol), N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (Example 26, Step B, 120 mg, 0.39 mmol, HPLC RT=2.25 min, method A), and HOBt hydrate (60 mg, 0.39 mmol) in DMF (3 mL) was added EDC (98 mg, 0.51 mmol). Diisopropylethylamine was then added slowly in portions (˜0.05 mL total) to bring the pH of the solution to 6–7 as measured on wetted E. Merck pH indicator strips. The mixture was stirred at ambient temperature for 18 h, and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (10 mL). The EtOAc layer was separated, dried over anhydrous MgSO4, and filtered. The filtrate solvent was removed under reduced pressure and the residue was purified by pressurized silica gel column chromatography using EtOAc as eluant. Product-containing fractions were combined and the solvent was removed under reduced pressure to give the title compound as an amorphous solid (TLC Rf=0.6 (EtOAc); HPLC RT=2.82 min, method A; LCMS m/z=441).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (10 mL)
  3. customThe EtOAc layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate solvent was removed under reduced pressure
  7. customthe residue was purified by pressurized silica gel column chromatography
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-af0357fa4f2549acbc445f07925b96da
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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