Diethylamine → HCID 18700176, compound

HRID 2289349Notes

Reaction equation

HRID 2289349 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:8]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[CH:7]=1)[CH:2]1[O:4][CH2:3]1.[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24]>CO>[CH2:23]([N:25]([CH2:26][CH3:27])[CH2:3][CH:2]([OH:4])[CH2:1][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:8]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[CH:7]=1)[CH3:24]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 53968277Methyl 4-(glycidyloxy)-2-(2,2,2-trifluoroethoxy)-phenylacetate

Product 1

HCID 18700176HCID 18700176, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(glycidyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetate (0.25 g, 0.81 mmol) from Step 1 of Example 34 in MeOH (3 mL) was added diethylamine (0.5 mL). The solution was kept at ambient temperature for 12 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (50 mL) and water (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give methyl 4-(3-diethylamino-2-hydroxypropyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetate as a pale yellow oil (HPLC retention time=6.9 min (method A); TLC Rf =0.23 (95:5 CH2Cl2 :MeOH)).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc (50 mL) and water (25 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4b47ab51e6a74d4aa29e1b0e5e6cd717
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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