Triethylamine → HCID 66735700, compound

HRID 1528613Notes

Reaction equation

HRID 1528613 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][CH2:23][CH2:24][C:25]([CH2:31][CH:32]2[CH2:34][CH2:33]2)([OH:30])[CH2:26][C:27]([CH3:29])=[CH2:28])[CH3:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([C@@H:20]([N:22]2[CH2:23][CH2:24][C:25]([CH2:31][CH:32]3[CH2:34][CH2:33]3)([CH2:26][C:27]([CH3:29])=[CH2:28])[O:30][C:2]2=[O:4])[CH3:21])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67997442HCID 67997442, compound

Product 1

HCID 66735700HCID 66735700, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphosgene (653 mg) was added to a solution of 1-[(S)-1-(4-bromophenyl)ethylamino]-3-(cyclopropylmethyl)-5-methylhex-5-en-3-ol (800 mg) and triethylamine (667 mg) in CH2Cl2 (15 mL) at 0° C. The mixture was stirred at room temperature overnight and the reaction was then quenched with water. The resulting mixture was extracted with CH2Cl2 and the combined organic layer was washed with brine and dried (Na2SO4). The solvent was evaporated and the residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 3:1) to afford the title compound. Yield 670 mg (78% of theory).

Workup

  1. customthe reaction was then quenched with water
  2. extractionThe resulting mixture was extracted with CH2Cl2
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-b81737f02b4742c6bd7a7998c33245b4
Source dataset
uspto-grants-2015_07
Patent number
US09090605B2

Reaction notes

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