Diisopropylethylamine → HCID 57859992, compound

HRID 1947166Notes

Reaction equation

HRID 1947166 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[N:29]([CH3:30])[C:28]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N:21]([CH2:31][C:32](=[O:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:20](=[O:40])[C:19]=3[C:18]=2[O:41][CH3:42])=[O:16])[CH:10]([CH3:43])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:42][O:41][C:18]1[C:19]2[C:20](=[O:40])[N:21]([CH2:31][C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:28]=2[N:29]([CH3:30])[C:17]=1[C:15]([NH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[CH3:43])=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformate2×HCID 57860268HCID 57860268, compound

Product 1

HCID 57859992HCID 57859992, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 677 (373 mg, 0.65 mmol) in THF (40 mL) was added 1-chloroethyl chloroformate (0.67 mL, 6.5 mol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. 1-Chloroethyl chloroformate (0.67 mL, 6.5 mol) and diisopropylethylamine (0.30 mL, 3.2 mmol) were added under ice-cooling, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, and the residue was washed with diethyl ether. The residue was dissolved in methanol (50 mL), and the mixture was stirred at room temperature for 7 hr and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; methanol/ethyl acetate=0/100-10/90) and recrystallized from ethyl acetate-hexane to give the title compound (90 mg, 29%) as a pale-brown solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 20 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. washthe residue was washed with diethyl ether
  6. dissolutionThe residue was dissolved in methanol (50 mL)
  7. stirringthe mixture was stirred at room temperature for 7 hr
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by aminosilica gel chromatography (eluate; methanol/ethyl acetate=0/100-10/90)
  10. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-83a32cca5d4b454f95c56b3b43ee6ac1
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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