Diisopropylethylamine → HCID 14403876, compound

HRID 1194144Notes

Reaction equation

HRID 1194144 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:14][CH3:15])[CH2:9][CH2:10][NH:11][CH2:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:27]>O1CCCC1>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][C:26](=[O:27])[N:11]([CH2:12][CH3:13])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:14][CH3:15])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 82128Carbonochloridic acid, 4-methoxyphenyl esterHCID 14403878HCID 14403878, compound

Product 1

HCID 14403876HCID 14403876, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-tert.-butoxycarbonyl-N,N'-diethylethylenediamine (3.22 g, 15 mmol) and N,N-diisopropylethylamine (2.6 mL, 15 mmol) in tetrahydrofuran (100 mL) was added over 1 hour to a stirred, cooled solution of 4-methoxyphenyl chloroformate (2.78 g, 15 mmol) in tetrahydrofuran (50 mL). After stirring at 20°-25° overnight, solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic extract was washed with brine, dried (Na2SO4), filtered and concentrated. Flash chromatography of the residue over silica gel and elution with 10-20% ethyl acetate-90-80% n-butylchloride gave 3.53 g of the carbamate as an oil.

Workup

  1. customsolvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washFlash chromatography of the residue over silica gel and elution with 10-20% ethyl acetate-90-80% n-butylchloride

Sources & evidence

ORD record
ord-7f0142ac4b714df28f1bd063aded8286
Source dataset
uspto-grants-1989_03
Patent number
US04812590

Reaction notes

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