Triphosgene → HCID 53241834, compound

HRID 1023611Notes

Reaction equation

HRID 1023611 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[NH2:19])=[CH:12][CH:11]=1.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl>C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:17](=[O:22])[C:18]([CH3:20])([CH3:21])[NH:19][C:24]2=[O:26])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 67235510HCID 67235510, compound2×

Product 1

HCID 53241834HCID 53241834, compoundYield 207.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

N1-{4-[(2,3-dimethylphenyl)oxy]phenyl}-2-methylalaninamide (Intermediate 76, 68 mg) was solved in 2 mL of ethyl acetate under nitrogen atmosphere. TEA (0.070 mL, 0.50 mmol) was added followed by a solution of triphosgene (33.8 mg, 0.11 mmol) in 1.0 mL of ethyl acetate. After stirring for 5 minutes, DMAP (13.9 mg, 0.11 mmol) was added and the reaction mixture was stirred at room temperature for 10 minutes. After quenching with a saturated solution of NaHCO3, the mixture was extracted two times with ethyl acetate, and the collected organic were dried over sodium sulphate, filtered and evaporated. The residue obtained was purified by silica gel chromatography eluting with a gradient cHex/EtOAc from 100/0 to 0/100. This afforded the title compound (74 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 10 minutes
  2. customAfter quenching with a saturated solution of NaHCO3
  3. extractionthe mixture was extracted two times with ethyl acetate
  4. dry with materialthe collected organic were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customwas purified by silica gel chromatography
  9. washeluting with a gradient cHex/EtOAc from 100/0 to 0/100

Sources & evidence

ORD record
ord-f75e4e3facb943b183a02e766638502d
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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