1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl N-((6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetyl)glycinate

HRID 591476Notes

Reaction equation

HRID 591476 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[C:10]([CH2:13][C:14](O)=[O:15])=[CH:11][S:12][C:8]=2[CH:7]=1.Cl.[NH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C([O-])(O)=O.[Na+].O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[C:10]([CH2:13][C:14]([NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:15])=[CH:11][S:12][C:8]=2[CH:7]=1

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2723640Glycine ethyl ester, hydrochlorideHCID 89767783(6-((2,4-Dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetic acid

Product 1

HCID 89767793Ethyl N-((6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetyl)glycinateYield 85.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of (6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetic acid (150 mg) in DMF (dry) (3.0 mL) were added ethyl 2-aminoacetate hydrochloride (57.0 mg), HOBt (71.7 mg), EDCI (102 mg) and triethylamine (0.171 mL). The mixture was stirred at room temperature for 17 h. The mixture was diluted with saturated aqueous NaHCO3 and water. The mixture was extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was washed with hexane to give the title compound (158 mg).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe combined organic layer was washed successively with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-adb28dc506054ce58ed7089073cf0241
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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