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

HRID 1621178Notes

Reaction equation

HRID 1621178 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-857486fa2ecb4ebca3fc49116cbb0e3a
Source dataset
uspto-grants-2014_07
Patent number
US08772536B2

Reaction notes

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