Triethylamine → 6-methoxy-3-phenyl-1-propionylamino-1H-indene-2-carboxylic acid ethyl ester

HRID 19560Notes

Reaction equation

HRID 19560 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH2:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[C:24](Cl)(=[O:27])[CH2:25][CH3:26].C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chloride2×HCID 116739651-amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 115088626-methoxy-3-phenyl-1-propionylamino-1H-indene-2-carboxylic acid ethyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (50 mg, 0.16 mmol) prepared in Example 20 was dissolved in dichloromethane (10 mL), and propionyl chloride (150.38 mg, 0.14 mL, 1.62 mmol) and triethylamine (180.12 mg, 0.25 mL, 1.78 mmol) were added thereto in order at 0° C. The mixture was stirred for 24 hrs at RT, and an excess amount of propionyl chloride (2 mL) was further added thereto to be stirred for 15 hrs. The resulting mixture was washed with saturated saline and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 29 mg of the titled compound (yield: 50%).

Workup

  1. customat 0° C
  2. stirringto be stirred for 15 hrs
  3. washThe resulting mixture was washed with saturated saline
  4. extractionextracted with dichloromethane
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e3b1b261e3074333bea20c1dd6c7cfe8
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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