Dimethylformamide → 2-(3-Acetoxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

HRID 521440Notes

Reaction equation

HRID 521440 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=O)(=[O:3])[CH3:2].CN(C=O)C.C(Cl)(=O)C(Cl)=O.Cl.[CH3:28][O:29][C:30]([C:32]1([NH2:41])[CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33]1)=[O:31].C(=O)([O-])O.[Na+]>C(Cl)Cl.CC(=O)OCC>[CH3:28][O:29][C:30]([C:32]1([NH:41][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33]1)=[O:31]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 151620Benzoic acid, 3-(acetyloxy)-4-methoxy-HCID 516892Sodium BicarbonateHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochloride

Product 1

HCID 670765742-(3-Acetoxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl esterYield 98.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3-Acetoxy-4-methoxy-benzoic acid (5.00 g, 23.8 mmol) was dissolved in DCM (50 ml). DMF (167 mg, 2.38 mmol) and oxalyl chloride (35.6 ml of a 2 M solution in DCM) were added at room temperature. The mixture was stirred for 20 min, evaporated to dryness in vacuo, the residue redissolved in DCM and evaporated again. The residue was dissolved in DCM and slowly added to a stirred mixture of 2-amino-indane-2-carboxylic acid methyl ester hydrochloride (5.42 g, 23.8 mmol), EA and an excess of a saturated aqueous sodium hydrogencarbonate solution. After 90 min the organic layer was separated and washed with a saturated sodium hydrogencarbonate solution, 2 M hydrochloric acid and a saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness to give 8.95 g of the title compound.

Workup

  1. customevaporated to dryness in vacuo
  2. dissolutionthe residue redissolved in DCM
  3. customevaporated again
  4. dissolutionThe residue was dissolved in DCM
  5. customAfter 90 min the organic layer was separated
  6. washwashed with a saturated sodium hydrogencarbonate solution, 2 M hydrochloric acid
  7. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-4e2bdad5267c4141acb93efb93c8f2f4
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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