Water → HCID 54179754, compound

HRID 342630Notes

Reaction equation

HRID 342630 reaction equation
[CH3:1][NH:2][C:3](=[O:23])[C:4]([N:6]([CH2:15][CH:16](OCC)[O:17]CC)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[CH3:14])=[O:5].O.FC(F)(F)C(O)=O.CCOC(C)=O>ClCCl>[CH3:1][NH:2][C:3](=[O:23])[C:4]([N:6]([CH2:15][CH:16]=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[CH3:14])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 131721071HCID 131721071, compound

Product 1

HCID 54179754HCID 54179754, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the ester from Step D (719 mg, 2.23 mmol) in 10 mL of dichloromethane at room temperature was added water (1 mL) and trifluoroacetic acid (1 mL). After 16 hours, the reaction was poured into EtOAc, washed with sat, NaHCO3 soln. and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the aldehyde (0.53 g, 100% yield) as a yellow oil which was sufficiently pure for use in the next step without further purification.

Workup

  1. washwashed
  2. dry with materialand brine, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c17d7c39d8a34681ba535e31e8269c36
Source dataset
uspto-grants-1999_01
Patent number
US05859012

Reaction notes

Loading…