N,N-Dimethylglycine → N,N-Dimethylglycine 2,3,4,5,6-pentafluorophenyl ester

HRID 446177Notes

Reaction equation

HRID 446177 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[F:8][C:9]1[C:14](O)=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=1[F:19].C1(N=C=NC2CCCCC2)CCCCC1>CCOC(C)=O>[F:8][C:9]1[C:14]([O:5][C:4](=[O:6])[CH2:3][N:2]([CH3:7])[CH3:1])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=1[F:19]

Participants

5

Reactant 3

HCID 673N,N-DimethylglycineHCID 10868DicyclohexylcarbodiimideHCID 13041Pentafluorophenol

Product 1

HCID 59882407N,N-Dimethylglycine 2,3,4,5,6-pentafluorophenyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 0.40 M solution of N,N-dimethylglycine (82.0 mg, 0.800 mmol) in EtOAc (2.00 mL, filtered through activated alumina) were added pentafluorophenol (162 mg, 0.880 mmol) and 1,3-dicyclohexylcarbodiimide (182 mg, 0.88 mmol). The reaction mixture was stirred for 12 h at rt at which time it was filtered (washing with EtOAc) and concentrated. Ester 18 was used immediately without further purification.

Workup

  1. filtrationwas filtered
  2. wash(washing with EtOAc)
  3. concentrationconcentrated
  4. customEster 18 was used immediately without further purification

Sources & evidence

ORD record
ord-97a906a7842e4d53ba6c965c1d0790a6
Source dataset
uspto-grants-2013_07
Patent number
US08476451B2

Reaction notes

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