Toluene → HCID 68539735, compound

HRID 655513Notes

Reaction equation

HRID 655513 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([C@H:19]([C:30]([O:32][CH3:33])=[O:31])[CH2:20][CH2:21][O:22]CC2C=CC=CC=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.B(Cl)(Cl)Cl>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([C@H:19]([C:30]([O:32][CH3:33])=[O:31])[CH2:20][CH2:21][OH:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 25135Boron Trichloride3×HCID 67074805HCID 67074805, compound

Product 1

HCID 68539735HCID 68539735, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.50 g (1.10 mmol) of 4-((S)-3-benzyloxy-1-methoxycarbonyl-propyl)-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester (evaporated twice with toluene) in 9 ml dichloromethane was treated with 1.10 ml (1.10 mmol, 1 M in dichloromethane) of boron trichloride. The solution was stirred 6.5 h at room temperature, cooled (0° C.) and treated with 0.99 ml (0.90 mmol, 1 M in dichloromethane) of boron trichloride, after 15 h at room temperature, additional 0.28 ml (0.28 mmol, 1 M in dichloromethane) of boron trichloride were added to the cooled (0° C.) reaction. After 24 h at room temperature, the mixture was extracted with cold sat. aq. sodium hydrogencarbonate solution and ethyl acetate (3×). The organic phases were washed with sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution, dried over Na2SO4 evaporated to give 0.298 g (75%) of the title compound as light yellow oil. MS: 365.0 (MH+).

Workup

  1. temperaturecooled (0° C.)
  2. temperaturecooled
  3. custom(0° C.) reaction
  4. waitAfter 24 h at room temperature
  5. extractionthe mixture was extracted with cold sat. aq. sodium hydrogencarbonate solution and ethyl acetate (3×)
  6. washThe organic phases were washed with sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-c11c85dde15746ca906668062ae65821
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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