Diisopropylethylamine → HCID 22644655, compound

HRID 2414310Notes

Reaction equation

HRID 2414310 reaction equation
[Cl:1]C(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[CH:15]=[CH:16][C:17](CO)=[C:18]([NH:20][CH:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[CH:19]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[ClH:1].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:7][O:6][C:5](=[O:11])[N:20]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:18]=2[CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 22644619HCID 22644619, compound

Product 1

HCID 22644655HCID 22644655, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphosgene (1.6 g) was added to a stirred solution of the product from step (i) (5 g), N,N-diisopropylethylamine (5.2 ml) in tetrahydrofuran (50 ml) at 0° C. The mixture was stirred at room temperature for 16 h, the precipitate filtered and the filtrate evaporated under reduced pressure. Purification was by chromatography eluting with 20% ethyl acetate/toluene. The product was dissolved in dichloromethane then a solution of hydrogen chloride in 1,4-dioxane added. After 2 h the solvent was removed under reduced pressure to yield a solid. Used directly.

Workup

  1. filtrationthe precipitate filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customPurification
  4. washeluting with 20% ethyl acetate/toluene
  5. dissolutionThe product was dissolved in dichloromethane
  6. additiona solution of hydrogen chloride in 1,4-dioxane added
  7. customAfter 2 h the solvent was removed under reduced pressure
  8. customto yield a solid

Sources & evidence

ORD record
ord-7ff984da44b649cdb086c1bb34d59d0d
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

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