Triethylamine → HCID 59485675, compound

HRID 1972261Notes

Reaction equation

HRID 1972261 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)[CH2:15][NH2:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:41](Cl)([O:43]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH:18]=4)[CH2:15][NH:16][C:41]3=[O:43])=[CH:9][CH:8]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 68704566HCID 68704566, compound

Product 1

HCID 59485675HCID 59485675, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the diamine (440 mg, 0.98 mmol) from Step 2, and triethylamine (330 μL, 2.4 mmol) in THF (20 mL) is added triphosgene (180 mg, 0.6 mmol) in THF at 0° C. After complete addition, the mixture is quenched with water and THF is removed by evaporation. The residue is extracted with ethyl acetate and washed with water. Evaporation of the organics gives a solid which is triturated with ethyl acetate, filtered, and washed with 40% ethyl acetate/hexane to give 279 mg of the title compound. Purification of the filtrate gives an additional 127 mg of product (combined yield, 88%). HPLC-MS calculated for C28H23ClN2O3 (M+H+): 471.1, found 471.1.

Workup

  1. additionAfter complete addition
  2. customthe mixture is quenched with water and THF
  3. customis removed by evaporation
  4. extractionThe residue is extracted with ethyl acetate
  5. washwashed with water
  6. customEvaporation of the
  7. customorganics gives a solid which
  8. customis triturated with ethyl acetate
  9. filtrationfiltered
  10. washwashed with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c1316b724b89436dad8c8559831bb947
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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