3,4-dihydro-2H-pyran → HCID 131733596, compound

HRID 1749539Notes

Reaction equation

HRID 1749539 reaction equation
[CH3:1][C:2]1([CH3:22])[C@@H:5]([C:6]2[N:10]=[CH:9][NH:8][N:7]=2)[CH2:4][C@H:3]1[NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1.CC1C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]1([CH3:22])[C@@H:5]([C:6]2[N:10]=[CH:9][N:8]([CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][O:23]3)[N:7]=2)[CH2:4][C@H:3]1[NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 178427884HCID 178427884, compound

Product 1

HCID 131733596HCID 131733596, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl ((1R,3S)-2,2-dimethyl-3-(1H-1,2,4-triazol-3-yl)cyclobutyl)carbamate (380 mg, 1.26 mmol), and 3,4-dihydro-2H-pyran (127 mg, 1.51 mmol) in dry DCM (10 mL) was added pyridinium 4-methylbenzenesulfonate (476 mg, 1.89 mmol). The mixture was refluxed overnight. After removal of the solvent, the residue was purified by silica gel column chromatography (12% ethyl acetate in petroleum ether) to afford the title compound (438 mg, 1.14 mmol, 90% yield). MS (ESI) m/z 385.4 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customAfter removal of the solvent
  3. customthe residue was purified by silica gel column chromatography (12% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-81fb66ad106045ae85b8ccae2fc8fc26
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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