m-Tolyl isocyanate → HCID 19037591, compound

HRID 375284Notes

Reaction equation

HRID 375284 reaction equation
[C:1]([N:5]([N:9]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH:11]([NH2:28])[C:10]1=[O:29])[C:6](=[O:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1([CH3:39])[CH:35]=[CH:34][CH:33]=[C:32]([N:36]=[C:37]=[O:38])[CH:31]=1>C(OCC)(=O)C>[C:1]([N:5]([N:9]1[CH:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH:11]([NH:28][C:37]([NH:36][C:32]2[CH:31]=[C:30]([CH3:39])[CH:35]=[CH:34][CH:33]=2)=[O:38])[C:10]1=[O:29])[C:6](=[O:8])[CH3:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19037623HCID 19037623, compound

Product 1

HCID 19037591HCID 19037591, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 35 mL round-bottomed flask equipped with N2 inlet and condenser were added 293 mg (0.745 mmol) (-)-1-(N-t-butylacetamido)-3-amino-5,7-diphenylhexahydroazepin-2-one, 10 mL ethyl acetate, and 0.096 mL (0.745 mmol) m-tolylisocyanate. The reaction was refluxed for 2.5 hr, cooled, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to afford an oil which was crystallized from methylene chloride/isopropyl ether to a give mp 140°-150° C., 71 mg (18%), αD =-18.6° (c=1, CH2Cl2). The Rf value on TLC and 1H-NMR spectrum match those of the racemate.

Workup

  1. customTo a 35 mL round-bottomed flask equipped with N2 inlet and condenser
  2. temperatureThe reaction was refluxed for 2.5 hr
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. customto afford an oil which
  7. customwas crystallized from methylene chloride/isopropyl ether to a give mp 140°-150° C., 71 mg (18%), αD =-18.6° (c=1, CH2Cl2)

Sources & evidence

ORD record
ord-b8985e19b2404173af4af3fd9d9c45d7
Source dataset
uspto-grants-1996_01
Patent number
US05484917

Reaction notes

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