Triethylamine → HCID 59505433, compound

HRID 1253655Notes

Reaction equation

HRID 1253655 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C@H:10]1[C:18]2[C:13](=[CH:14][C:15]([CH3:22])=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=2)[CH2:12][CH2:11]1.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C(Cl)Cl>[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH:9][C@H:10]1[C:18]2[C:13](=[CH:14][C:15]([CH3:22])=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=2)[CH2:12][CH2:11]1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 66701112HCID 66701112, compound

Product 1

HCID 59505433HCID 59505433, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (4.707 mmol, 1.5 eq.) was added to a solution of (R)-3-amino-6-methyl-2,3-dihydro-1H-indene-5-carboxylic acid hydrochloride (commercially available from NetChem) (1 eq., 3.138 mmol) in methylene chloride (16 ml) at 0° C. 2-Chlorobenzoyl chloride (1.2 eq.) was added dropwise to the reaction mixture at the same temperature and the mixture was stirred for 16 h at room temperature. The reaction mixture was diluted with methylene chloride (50 ml), and washed with NH4Cl solution (20 ml) and sat. NaCl solution (20 ml). The organic phase was dried over magnesium sulfate and the solvent was removed in vacuo. The crude material was purified by column chromatography (silica, ethyl acetate/cyclohexane 3:2) to yield the desired product (E-12). Yield: 43%

Workup

  1. washwashed with NH4Cl solution (20 ml) and sat. NaCl solution (20 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe crude material was purified by column chromatography (silica, ethyl acetate/cyclohexane 3:2)

Sources & evidence

ORD record
ord-7f7a82d77e564fbcac7b29d44d88ded6
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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