1,2-Dichloroethane → HCID 66611389, compound

HRID 2204711Notes

Reaction equation

HRID 2204711 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:10]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[CH:11][C:12]([C:18]([F:21])([F:20])[F:19])=[C:13]([CH:17]=2)[C:14](O)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O.O.C(OCC)(=O)C>[N:41]1([C:14]([C:13]2[C:12]([C:18]([F:21])([F:19])[F:20])=[CH:11][C:10]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])=[C:9]([O:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:17]=2)=[O:15])[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66612055HCID 66612055, compound

Product 1

HCID 66611389HCID 66611389, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(phenylmethyl)oxy]-4-{[(phenylmethyl)oxy]carbonyl}-2-(trifluoromethyl)benzoic acid (may be prepared as described in Description 55; 71 mg, 0.16 mmol) in N,N-dimethylformamide (4 ml) was added diisopropylethylamine (0.07 ml, 0.39 mmol), morpholine (0.03 ml, 0.29 mmol), 1-hydroxy-7-azabenzotriazole (34.2 mg, 0.25 mmol) and EDC (66.6 mg, 0.35 mmol). The mixture was stirred at room temperature for 18 hours. Ethyl acetate (10 ml) and water (10 ml) were added and the organic layer was separated, washed with water (2×10 ml), dried (MgSO4) and solvent removed in vacuo. Purification by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane) gave the title compound as a solid. 66 mg.

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×10 ml)
  3. dry with materialdried (MgSO4) and solvent
  4. customremoved in vacuo
  5. customPurification by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-666081afb4474dbab6e2d3fce0412a5b
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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