Triethylamine → Hydrochloric Acid

HRID 1956687Notes

Reaction equation

HRID 1956687 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[C:12]([CH2:13][NH:14][CH:15]([CH2:25][C:26]#[C:27][CH3:28])[CH2:16][NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[Cl:38][C:39](Cl)([O:41]C(=O)OC(Cl)(Cl)Cl)Cl.CCOC(C)=O>C1COCC1>[ClH:24].[CH2:25]([CH:15]1[CH2:16][N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C:39](=[O:41])[N:14]1[CH2:13][C:12]1[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:30][CH:29]=2)[CH:9]=[N:10][CH:11]=1)[C:26]#[C:27][CH3:28].[ClH:38]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 67644443HCID 67644443, compound

Product 2

HCID 313Hydrochloric AcidYield 548.5%HCID 9913031HCID 9913031, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product from Step M (75 mg, 0.14 mmol) in 1.0 mL of THF at 0° C. was added triethylamine (0.12 mL, 0.89 mmol), followed by triphosgene (26 mg, 0.088 mmol). The reaction was stirred at 0° C. for two hours, then poured into EtOAc and washed with sat. aq. NaHCO3 and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by silica gel chromatography (50-75% acetone/hexane), taken up in CH2Cl2 and treated with 1M HCl/ether solution, and concentrated in vacuo. The titled product hydrochloride (14 mg) was isolated as an orange powder.

Workup

  1. washwashed with sat. aq. NaHCO3 and brine
  2. dry with materialThe solution was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by silica gel chromatography (50-75% acetone/hexane)
  6. additiontreated with 1M HCl/ether solution
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de60f46d708e4890acd2ca4cdb05829f
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

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