Triethylamine → HCID 131720124, compound

HRID 2258026Notes

Reaction equation

HRID 2258026 reaction equation
[NH2:1][CH:2]([CH:8]([C:18]1[CH:26]=[CH:25][C:21]2[O:22][CH2:23][O:24][C:20]=2[CH:19]=1)[C:9]1[CH:17]=[CH:16][C:12]2[O:13][CH2:14][O:15][C:11]=2[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:27]1([CH:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[O:22]1[C:21]2[CH:25]=[CH:26][C:18]([CH:8]([C:9]3[CH:17]=[CH:16][C:12]4[O:13][CH2:14][O:15][C:11]=4[CH:10]=3)[CH:2]([NH:1][C:34](=[O:35])[CH:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:19][C:20]=2[O:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 746372,2-Diphenylacetyl chlorideHCID 131720123HCID 131720123, compound

Product 1

HCID 131720124HCID 131720124, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The amino ester of Example 19 (0.510 g, 1.43 mmol) is mixed with diphenylacetyl chloride (0.346 g, 1.5 mmol) in 20 mL of dry chloroform. Triethylamine (0.6 mL, 4.3 mmol) is added to the reaction mixture and it is stirred for 2 hours. The solvent is evaporated and the residue is taken up into 75 mL of ethyl acetate. The solution is washed with 1N hydrochloric acid and saturated sodium bicarbonate respectively. The organic phase is dried (magnesium sulfate), filtered and purified by a short column to afford 0.552 g (70%) of product as a white solid;

Workup

  1. customThe solvent is evaporated
  2. washThe solution is washed with 1N hydrochloric acid and saturated sodium bicarbonate respectively
  3. dry with materialThe organic phase is dried (magnesium sulfate)
  4. filtrationfiltered
  5. custompurified by a short column

Sources & evidence

ORD record
ord-6d33e7cff9d342f6b9f054f521a42682
Source dataset
uspto-grants-1997_08
Patent number
US05658943

Reaction notes

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