2-Chlorobenzoyl chloride → HCID 59505264, compound

HRID 1193266Notes

Reaction equation

HRID 1193266 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.CCN(C(C)C)C(C)C.[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29]>ClCCl.[Cl-].[NH4+].C(OCC)(=O)C>[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([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:29]

Participants

7

Reactant 3

HCID 691102-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 67546135Methyl (1R)-1-aminoindane-5-carboxylate hydrochloride

Product 1

HCID 59505264HCID 59505264, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

(R)-Methyl 1-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride (A-02) (0.661 mmol, 1 eq) was dissolved in dichloromethane and DIPEA (2.5 eq) under a protecting gas atmosphere, and 2-chlorobenzoic acid chloride (1 eq) was added at 0° C. The reaction mixture was stirred for 2 h at RT. Then the reaction mixture was diluted with 10% ammonium chloride solution and ethyl acetate, and the phases were separated. The organic phase was washed with sat. NaCl solution, dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, cyclohexane:ethyl acetate 2:1) to yield (R)-methyl 1-(2-chlorobenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-02). Yield: 74%

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with sat. NaCl solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (silica gel, cyclohexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-3e3549bb49a64e75a071f6ab72a00bf6
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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