4-Methylmorpholine → HCID 69285669, compound

HRID 2225210Notes

Reaction equation

HRID 2225210 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:15]([O:19][C:20](=[O:23])[CH2:21][NH2:22])([CH3:18])([CH3:17])[CH3:16].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([NH:22][CH2:21][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:23])=[O:6]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 151417Glycine tert-butyl esterHCID 6882922-Fluoro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 69285669HCID 69285669, compoundYield 178.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Preparation I7, Step 1: A solution of 2-fluoro-5-trifluoromethylbenzoic acid (5.80 g) in N,N-dimethylformamide (190 mL) was treated sequentially with glycine t-butyl ester (5.50 g), BOP reagent (18.50 g), and N-methylmorpholine (9.20 mL). The mixture was stirred at rt for 12 h, then was diluted with ethyl acetate. The organic layer was washed with 1 M HCl, saturated aqueous NaHCO3, 5% aqueous LiCl, and brine, then was dried over Na2SO4 and concentrated under vacuum to provide tert-butyl 2-(2-fluoro-5-(trifluoromethyl)benzamido)acetate (16 g) as a white solid. MS found: (M+H)+=322.

Workup

  1. customPreparation I7, Step 1
  2. washThe organic layer was washed with 1 M HCl, saturated aqueous NaHCO3, 5% aqueous LiCl, and brine
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-86b19f554e7b4e8e81b5229ede9f693e
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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