1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl [(2,3-difluorobenzoyl)amino]acetate

HRID 539588Notes

Reaction equation

HRID 539588 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:13][O:14][C:15](=[O:18])[CH2:16][NH2:17].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>O1CCCC1>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:17][CH2:16][C:15]([O:14][CH3:13])=[O:18])=[O:6]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 3705902,3-Difluorobenzoic acid

Product 1

HCID 59816250Methyl [(2,3-difluorobenzoyl)amino]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-difluorobenzoic acid (0.190 g, 1.2 mmol) in tetrahydrofuran (5 mL) were added glycine methyl ester hydrochloride (0.150 g, 1.2 mmol), HOBt (0.162 g, 1.2 mmol), DIEA (0.209 mL, 1.2 mmol) and EDCI (0.252 g, 1.3 mmol). The reaction mixture was allowed to stir overnight. The reaction mixture was quenched with a saturated solution of sodium bicarbonate and the product partitioned into DCM. Separation of the organic layer followed by removal of the solvent gave methyl [(2,3-difluorobenzoyl)amino]acetate which was used in the next step without purification.

Workup

  1. customThe reaction mixture was quenched with a saturated solution of sodium bicarbonate
  2. customthe product partitioned into DCM
  3. customSeparation of the organic layer
  4. customfollowed by removal of the solvent

Sources & evidence

ORD record
ord-9efd818d8ed84bebab2c12acc271580a
Source dataset
uspto-grants-2014_10
Patent number
US08871745B2

Reaction notes

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