Triethylamine → HCID 68588340, compound

HRID 1875349Notes

Reaction equation

HRID 1875349 reaction equation
[N:1]1[CH:7]=[CH:6][C:5](=[O:8])[N:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>C(Cl)Cl>[O:8]=[C:5]1[CH:6]=[CH:7][N:1]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:2][CH:3]=[N:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 22288339HCID 22288339, compound

Product 1

HCID 68588340HCID 68588340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.8 g (42.0 mmol) [1,4]diazepin-5-one are dissolved in 60 ml DCM and at ice bath temperature successively combined with 11.0 ml (83.9 mmol) triethylamine and 6.8 ml (46.2 mmol) benzyl chloroformate. The mixture is heated to RT and kept for three hours at this temperature. Then the mixture is concentrated and combined with water. The aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac. The crude product is [purified] by column chromatography on silica gel (eluant DCM/MeOH 95:5→90:10).

Workup

  1. concentrationThen the mixture is concentrated
  2. extractionThe aqueous phase is extracted three times with ethyl acetate
  3. customThe combined organic phases are dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. custom[purified] by column chromatography on silica gel (eluant DCM/MeOH 95:5→90:10)

Sources & evidence

ORD record
ord-64ea7020a94548d4997eccf03ba194a8
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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