Diisopropylethylamine → HCID 123597098, compound

HRID 627152Notes

Reaction equation

HRID 627152 reaction equation
[CH2:1]([O:4][NH:5][C@H:6]1[C:11]([CH2:12][O:13][CH3:14])=[CH:10][CH:9]([CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[NH:8][CH2:7]1)[CH:2]=[CH2:3].C(N(C(C)C)C(C)C)C.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C.CCOC(C)=O>[CH2:1]([O:4][N:5]1[C:34](=[O:36])[N:8]2[CH2:7][CH:6]1[C:11]([CH2:12][O:13][CH3:14])=[CH:10][C@H:9]2[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 131735283HCID 131735283, compound

Product 1

HCID 123597098HCID 123597098, compoundYield 193.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Intermediate 121 (2.04 g, 5.96 mmol) in acetonitrile (500 mL), N-ethyl-N-isopropylpropan-2-amine (4.15 mL, 23.82 mmol) was added triphosgene (0.721 g, 2.38 mmol) as a solution in 20 mL CH3CN via syringe pump (0.1 ml/min) at 0° C. The reaction was stirred and allowed to warm from 0° C. to rt overnight. LCMS showed complete conversion to product. The solution was concentrated to give a residue, which was then taken up in 150 mL EtOAc and washed with 5% citric acid, NaHCO3, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column (40 g, 0-60% Hex/EA) to afford the title compound (1.700 g, 77%) as an oil.

Workup

  1. temperatureto warm from 0° C. to rt overnight
  2. concentrationThe solution was concentrated
  3. customto give a residue, which
  4. washwashed with 5% citric acid, NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (40 g, 0-60% Hex/EA)

Sources & evidence

ORD record
ord-8cb4e4f93f36472a9a29da9a619b96c3
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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