Diisopropylethylamine → HCID 59505295, compound

HRID 1253648Notes

Reaction equation

HRID 1253648 reaction equation
C(N(C(C)C)C(C)C)C.[Cl:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[S:18](Cl)(=[O:20])=[O:19].Cl.[CH3:23][O:24][C:25]([C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[CH2:32][CH2:31][C@H:30]2[NH2:36])=[O:26]>C(Cl)Cl.C(OCC)(=O)C>[Cl:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[S:18]([NH:36][C@H:30]1[C:29]2[C:33](=[CH:34][CH:35]=[C:27]([C:25]([O:24][CH3:23])=[O:26])[CH:28]=2)[CH2:32][CH2:31]1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 66700566(R)-methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride

Product 1

HCID 59505295HCID 59505295, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Ethyl-diisopropylamine (2.5 eq.) and 2,3-dichlorobenzene-1-sulfonyl chloride (1.2 eq.) were added to an ice-cold solution of (3R)-3-amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-03 HCl) (0.88 mmol, 1 eq.) in methylene chloride at 0° C. under an inert atmosphere. The mixture was then stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate and the organic phase was washed with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution. The organic phase was dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (silica, cyclohexane/ethyl acetate, 2:1) to yield the desired compound (C-06). Yield: 97%

Workup

  1. washthe organic phase was washed with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (silica, cyclohexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-2401d624b17c4605826c4abdf4839d3b
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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