Triethylamine → HCID 59505430, compound

HRID 1253647Notes

Reaction equation

HRID 1253647 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15](Cl)(=[O:17])=[O:16].Cl.[CH3:20][O:21][C:22]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[CH2:29][CH2:28][C@H:27]2[NH2:33])=[O:23]>C(Cl)Cl.C(OCC)(=O)C>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:33][C@H:27]1[C:26]2[C:30](=[CH:31][CH:32]=[C:24]([C:22]([O:21][CH3:20])=[O:23])[CH:25]=2)[CH2:29][CH2:28]1)(=[O:17])=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 66700566(R)-methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride

Product 1

HCID 59505430HCID 59505430, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamin (2.195 mmol, 2,5 eq.) and 2-chlorobenzene-1-sulfonyl chloride (0,878 mmol, 1 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) (0.878 mmol, 1 eq.) in methylene chloride under an inert atmosphere. The mixture was then stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate (50 ml) and the organic phase was washed with 10% NH4Cl solution (20 ml), sat. NaHCO3 solution (20 ml) and sat. NaCl solution (20 ml). The organic phase was dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography over silica gel (cyclohexane/ethyl acetate, 2:1) to obtain the desired product. Yield: >99%

Workup

  1. washthe organic phase was washed with 10% NH4Cl solution (20 ml), sat. NaHCO3 solution (20 ml) and sat. NaCl solution (20 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography over silica gel (cyclohexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-36d4fe05beae43edade40ab33cdf0ca5
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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