Triethylamine → HCID 57410106, compound

HRID 527684Notes

Reaction equation

HRID 527684 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:23])[C@@H:20]([CH3:22])[NH2:21])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.C(N(CC)CC)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl>C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[CH3:22][C@H:20]1[NH:21][C:32](=[O:34])[N:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][C:7]3[C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH:10]=[CH:9][CH:8]=3)=[CH:13][CH:14]=2)[C:19]1=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67966819HCID 67966819, compound2×

Product 1

HCID 57410106HCID 57410106, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

N1-{4-[(3-methyl-1,2-benzisoxazol-4-yl)oxy]phenyl}-D-alaninamide (Intermediate 14, 337 mg) was dissolved in 8.0 ml of ethyl acetate. Triethylamine (0.33 ml, 2.38 mmol) was added followed by a solution of triphosgene (161 mg, 0.54 mmol) in 2.0 ml of ethyl acetate. After 5 minutes stirring, DMAP (66 mg, 0.54 mmol) was added and the reaction mixture was stirred at room temperature for 10 minutes. After quenching with a saturated aqueous solution of NaHCO3, the reaction mixture was extracted two times with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with a gradient Cy-Hex/EtOAc from 100/0% to 0/100%. This afforded the title compound (160 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 10 minutes
  2. customAfter quenching with a saturated aqueous solution of NaHCO3
  3. extractionthe reaction mixture was extracted two times with ethyl acetate
  4. dry with materialThe gathered 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 Cy-Hex/EtOAc from 100/0% to 0/100%

Sources & evidence

ORD record
ord-e002733fbfd946dc8b7ee3237d174690
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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