Dichloromethane → HCID 69048900, compound

HRID 1293233Notes

Reaction equation

HRID 1293233 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]([NH:14]C(=O)OC(C)(C)C)[CH3:13])=[CH:8][CH:7]=1.FC(F)(F)C(O)=O.[Cl:29]CCl>>[ClH:29].[N:4]1[NH:3][N:2]=[N:1][C:5]=1[C:6]1[CH:7]=[CH:8][C:9]([C@@H:12]([NH2:14])[CH3:13])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57572302HCID 57572302, compound

Product 1

HCID 69048900HCID 69048900, compoundYield 83%

Procedure

tert-Butyl {(1S)-1-[4-(2H-tetrazol-5-yl)phenyl]ethyl}carbamate (step 2, 1.19 g, 4.10 mmol) was treated with trifluoroacetic acid (10 mL) and dichloromethane (10 mL) at room temperature for 1 h. After removal of the solvent, the residue was diluted with 4 M solution of hydrogen chloride in ethyl acetate (20 mL). The mixture was concentrated under reduced pressure and the residue was washed with ether to give 0.77 g (83%) of the title compounds as white solids: 1H-NMR (DMSO-d6) δ 8.60 (3H, br.s), 8.14 (2H, d, J=8.4 Hz), 7.75 (2H, d, J=8.4 Hz), 4.58–4.45 (1H, m), 1.55 (3H, d, J=6.8 Hz); MS (ESI) m/z 188 (M−H)−.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was diluted with 4 M solution of hydrogen chloride in ethyl acetate (20 mL)
  3. concentrationThe mixture was concentrated under reduced pressure
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-e393aaf2707346b6906e7c4e2bf34b26
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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