Oxalyl chloride → HCID 59314300, compound
Reaction equation
[O:1]1[C:5]2[C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[CH2:19]([O:21][C:22]([C:24]1([NH2:33])[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1)=[O:23])[CH3:20].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:19]([O:21][C:22]([C:24]1([NH:33][C:10]([C:6]2[C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=[CH:8][CH:7]=2)=[O:12])[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1)=[O:23])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,3-dihydro-benzofuran-7-carboxylic acid (394 mg, 2.4 mmol) in DCM (10 mL) is added oxalyl chloride (0.85 mL, 9.6 mmol). The resulting solution is stirred at RT for 2 h. After the removal of DCM and excess oxalyl chloride, the residue, 2-amino-indan-2-carboxylic acid ethyl ester (500 mg, 2.4 mmol) and DIPEA (3.17 mL, 19.2 mmol) are dissolved in DCM (20 mL). The resulting solution is stirred at RT overnight. The reaction solution is diluted with DCM (40 mL) and washed with water (1×5 mL) and brine (2×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 g silica gel, gradient elution: 0%-20% EtOAc in heptane) to give a pure product (39) as white solid (635 mg, 75%).
Workup
- customAfter the removal of DCM and excess oxalyl chloride
- stirringThe resulting solution is stirred at RT overnight
- washwashed with water (1×5 mL) and brine (2×5 mL)
- dry with materialThe organic layer is dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 0%-20% EtOAc in heptane)
Sources & evidence
- ORD record
- ord-f203d3d77bf448ffa6defc7818587ab4
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569535B2
Reaction notes
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