Dimethylformamide → Ethyl N-(thiophene-2-carbonyl)glycinate

HRID 1178073Notes

Reaction equation

HRID 1178073 reaction equation
CCN([CH:7]([CH3:9])C)C(C)C.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([OH:17])=O.C1C=CC2N([OH:27])N=NC=2C=1.CCN=C=NCCC[N:36]([CH3:38])C.Cl.CN([CH:43]=[O:44])C>O>[CH2:7]([O:27][C:43](=[O:44])[CH2:38][NH:36][C:15]([C:11]1[S:10][CH:14]=[CH:13][CH:12]=1)=[O:17])[CH3:9]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 107002-Thiophenecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 1720748Ethyl N-(thiophene-2-carbonyl)glycinateYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DIPEA (0.472 mL, 2.73 mmol) was added to a stirred solution of thiophene-2-carboxylic acid (100 mg, 0.78 mmol) in DMF (1 mL). HOBT (126 mg, 0.94 mmol) and EDCI.HCl (179 mg, 0.94 mmol) were added, followed by the addition of ethyl glycine ester hydrochloride (119 mg, 0.86 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. The mixture was then diluted with water and the product extracted with EtOAc. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford [(thiophene-2-carbonyl)-amino]-acetic acid ethyl ester in 84% yield, LC-MS purity: 97%

Workup

  1. extractionthe product extracted with EtOAc
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ad602b5b6da40e4b3275d6dce37e755
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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