HCID 59226411, compound → HCID 59226573, compound

HRID 2192561Notes

Reaction equation

HRID 2192561 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH:7]1[NH:21][C:22]([O:24]C(C)(C)C)=[O:23])(=O)=O>N1C=CC=CC=1>[N+:18]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:12]=1[C:9]1[CH2:10][CH2:11][CH:6]2[O:24][C:22](=[O:23])[NH:21][CH:7]2[CH:8]=1)([O-:20])=[O:19]

Participants

3

Reactant 1

HCID 59226411HCID 59226411, compound

Product 1

HCID 59226573HCID 59226573, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of (+/−)-2-(tert-butoxycarbonylamino)-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate (1.0 equiv.) in pyridine (0.21 M) was stirred at 110° C. for 10 min in microwave. Pyridine was removed under reduced pressure. The residue was dissolved in ethyl acetate, and washed with sat NaCl. The organic was dried with MgSO4, filtered and concentrated to give (+/−)-5-(3-nitropyridin-4-yl)-3,3a,7,7a-tetrahydrobenzo[d]oxazol-2(6H)-one (85%), which was used in the next step without further purification. LC/MS (m/z): MH+=262.1, Rt=0.49

Workup

  1. customPyridine was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed
  4. dry with materialThe organic was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-18c8ce51df934826ab1041e21f25e77b
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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