Triethylamine → HCID 59505712, compound

HRID 1193279Notes

Reaction equation

HRID 1193279 reaction equation
Cl.[NH2:2][C@H:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30](Cl)(=[O:32])=[O:31]>ClCCl>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH:2][C@H:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 67546135Methyl (1R)-1-aminoindane-5-carboxylate hydrochloride

Product 1

HCID 59505712HCID 59505712, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-Methyl 1-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride (A-02) (0.2 g, 0.881 mmol, 1 eq) was dissolved in dichloromethane and triethylamine (2.5 eq) under nitrogen, and 2-chlorobenzenesulfonic acid chloride (0.185 g, 0.881 mmol, 1 eq) was added at 0° C. The reaction mixture was stirred for 2 h at RT. Then concentration was carried out under reduced pressure, and the residue was diluted with ethyl acetate, washed with 10% ammonium chloride solution and sat. NaCl solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, cyclohexane:EA 4:1) and the desired product (R)-methyl 1-(2-chlorophenylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (C-01) was thus obtained. Yield: 87%

Workup

  1. concentrationThen concentration
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 10% ammonium chloride solution and sat. NaCl solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, cyclohexane:EA 4:1)

Sources & evidence

ORD record
ord-3434f36deb2a4d2f807f4d49f8039e0a
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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