1,2-Dichloroethane → N2-Benzyloxycarbonyl-N1-(2,2-dimethoxyethyl)-N1-(4-fluorobenzyl)-glycinamide

HRID 1162797Notes

Reaction equation

HRID 1162797 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[C:16]([NH:26][CH2:27][C:28](O)=[O:29])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(N(CC)C(C)C)(C)C>[CH2:19]([O:18][C:16]([NH:26][CH2:27][C:28]([N:5]([CH2:4][CH:3]([O:14][CH3:15])[O:2][CH3:1])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1)=[O:29])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 14349BenzyloxycarbonylglycineHCID 757711-HydroxybenzotriazoleHCID 11615438N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

Product 1

HCID 59813049N2-Benzyloxycarbonyl-N1-(2,2-dimethoxyethyl)-N1-(4-fluorobenzyl)-glycinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine (50.6 g, 237.3 mmol), N-CBZ-glycine (54.6 g, 260.8 mmol), EDC (50.0 g, 260.8 mmol), and HOBt (4.2 g, 27 mmol) in anhydrous DMF (500 mL), N,N-diisopropylethylamine (˜10 mL) was added until the solution is about pH 7. The reaction mixture was stirred at room temperature overnight and concentrated under vacuum. The residue was partitioned between dichloromethane (1 L) and water (250 mL). The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title compound. ES MS (M−OCH3)=374.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was partitioned between dichloromethane (1 L) and water (250 mL)
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-380ea47541144e6cb99477237759e517
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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