Triethylamine → HCID 59190391, compound

HRID 219626Notes

Reaction equation

HRID 219626 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][CH2:13][C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([OH:19])[CH2:15][C:16]([CH3:18])=[CH2:17])[CH3:9])=[CH:4][CH:3]=1.Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:11][CH2:12][CH2:13][C:14]([CH2:15][C:16]([CH3:18])=[CH2:17])([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:19][C:27]2=[O:29])[CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 591903777-((1S)-1-(4-bromophenyl)ethylamino)-2-methyl-4-phenylhept-1-en-4-ol

Product 1

HCID 59190391HCID 59190391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 7-((1S)-1-(4-bromophenyl)ethylamino)-2-methyl-4-phenylhept-1-en-4-ol (2.2 g, 5.5 mmol) in CH2Cl2 (50 mL) was added triphosgene (3.2 g, 11 mmol) and Et3N (1.7 g, 16.5 mmol) at 0° C. The mixture was stirred at room temperature overnight, and put at room temperature for 3 days, the volatile was evaporated. The resulting mixture was washed with 1 N aq HCl and extracted with CH2Cl2. The combined organic phase was dried over Na2SO4 and concentrated to give the crude final product, which was purified by chromatography to afford two isomers.

Workup

  1. waitput at room temperature for 3 days
  2. customthe volatile was evaporated
  3. washThe resulting mixture was washed with 1 N aq HCl
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5c12ae9a0d1049b9ab18eb4a9ad477e9
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Reaction notes

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