Nitrogen → HCID 178446037, compound

HRID 1180762Notes

Reaction equation

HRID 1180762 reaction equation
C([C:3](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:4]([C@@H:6]([NH:11][C:12](=[O:28])[O:13][C:14]1([C:19]2[S:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:7][CH2:8][CH2:9][CH3:10])=[O:5])#N.[O:48]=[O+][O-].N#N.[NH2:53][C:54]1[CH:58]=[CH:57][NH:56][N:55]=1>ClCCl.O1CCCC1>[O:48]=[C:3]([NH:53][C:54]1[CH:58]=[CH:57][NH:56][N:55]=1)[C:4]([C@@H:6]([NH:11][C:12](=[O:28])[O:13][C:14]1([C:19]2[S:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:7][CH2:8][CH2:9][CH3:10])=[O:5]

Participants

7

Reactant 4

HCID 947NitrogenHCID 24823OzoneHCID 58979683HCID 58979683, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 178446037HCID 178446037, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

660 mg (1 mmol) of 1-(1,3-benzothiazol-2-yl)cyclopentyl(1S)-1-[cyano(triphenylphosphoranylidene)acetyl]pentylcarbamate was dissolved in 25 mL of dichloromethane and ozone was passed through the solution at −78° C. for 15 min. The reaction was quenched with N2 for 5 min before 79 mg (0.95 mmol) of 3-aminopyrazole in 4 mL of tetrahydrofuran was added. The reaction was allowed to warm to room temperature over 1 h. Solvent was removed and the residue was redissolved in 5 mL of tetrahydrofuran. 1 mL of 1 M silver nitrate in water was added and the reaction was stirred at room temperature overnight. Water was added and the mixture was extracted with ether (4×). The ether layer was washed with brine (3×) and dried over magnesium sulfate. After removal of solvent, purification by silica gel column chromatography eluting with hexane:ethyl acetate (1:2) gave 150 mg (32%) of 1-(1,3-benzothiazol-2-yl)cyclopentyl(1S)-1-[oxo(1H-pyrazol-3-ylamino)acetyl]pentylcarbamate as a solid. 1H-NMR (400 MHz CDCl3) δ 7.87 (d, J=8 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.42 (s, 1H), 7.36 (t, J=8 Hz, 1H), 7.22 (m, 2H), 6.78 (s, 1H), 4.96 (br, 1H), 2.45 (m, 4H), 1.86 (m, 4H), 1.30 (m, 6H), 0.88 (t, J=8 Hz, 3H). ES-LCMS m/z 469 (M+H). C23H27N3O4S: 0.34 EtOAc: 0.13 H2O: Anal C 58.3%, H 5.93%, N 13.95%; Calcd C, 58.3%, H, 6.02%, N, 13.95%.

Workup

  1. additionwas added
  2. customSolvent was removed
  3. dissolutionthe residue was redissolved in 5 mL of tetrahydrofuran
  4. addition1 mL of 1 M silver nitrate in water was added
  5. additionWater was added
  6. extractionthe mixture was extracted with ether (4×)
  7. washThe ether layer was washed with brine (3×)
  8. dry with materialdried over magnesium sulfate
  9. customAfter removal of solvent, purification by silica gel column chromatography
  10. washeluting with hexane:ethyl acetate (1:2)

Sources & evidence

ORD record
ord-201deac2ed0c429ea193375ad89f13ed
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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