Triethylamine → HCID 57410107, compound

HRID 527685Notes

Reaction equation

HRID 527685 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:24])[C@@H:21]([CH3:23])[NH2:22])=[CH:15][CH:14]=3)=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[O:4][N:3]=1.C(N(CC)CC)C.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1[C:6]2[C:7]([O:12][C:13]3[CH:14]=[CH:15][C:16]([N:19]4[C:20](=[O:24])[C@@H:21]([CH3:23])[NH:22][C:33]4=[O:35])=[CH:17][CH:18]=3)=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[O:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67966817HCID 67966817, compound2×

Product 1

HCID 57410107HCID 57410107, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

N1-{4-[(3,6-dimethyl-1,2-benzisoxazol-4-yl)oxy]phenyl}-D-alaninamide (Intermediate 23, 54 mg) was dissolved in 7.0 ml of ethyl acetate. Then triethylamine (0.051 ml, 0.37 mmol) was added followed by a solution of triphosgene (24.6 mg, 0.083 mmol) in 2.0 ml of ethyl acetate. After stirring for 5 minutes, DMAP (10.1 mg, 0.083 mmol) was added and the reaction mixture was stirred at room temperature for 10 minutes. After quenching with an aqueous solution of NaHCO3, the mixture was extracted two times with ethyl acetate and the collected organic layers were dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with a gradient c-Hex/EtOAc from 100/0 to 0/100 to afford the title compound (11 mg)

Workup

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

Sources & evidence

ORD record
ord-16b1d400ebd34e20bedbed7495fa064c
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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