Triethylamine → HCID 58930724, compound

HRID 1181644Notes

Reaction equation

HRID 1181644 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.[F:13][C:14]([F:32])([C:28]([F:31])([F:30])[F:29])[C@@H:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][CH:20]=1)[CH3:16].CCN(CC)CC.CCOC(C)=O>C(O)=O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]([O:17][C@H:15]([C:14]([F:13])([F:32])[C:28]([F:30])([F:31])[F:29])[CH3:16])=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 546829304-HydroxycoumarinHCID 58930721HCID 58930721, compound

Product 1

HCID 58930724HCID 58930724, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
140 °C

Procedure

4-Hydroxycoumarin (1.367 g, 8.44 mmol) and (S)-4-formyl-benzoic acid 2,2,3,3,3-pentafluoro-1-methyl-propyl ester (2.505 g, 8.46 mmol) were dissolved in formic acid (3.0 mL) and Et3N (3.6 mL) at 0° C. After stirring at 140° C. for 4 h, the yellow solution was cooled to rt, EtOAc was added, and the organic layer was washed successively with 1 N HCl and brine. After drying over Na2SO4 and concentrating, the pale yellow solid was purified twice by silica gel chromatography (DCM:MeOH 100:6 and DCM:MeOH 100:5) to yield the title compound in 92.5% ee as determined by chiral HPLC.

Workup

  1. customat 0° C
  2. temperaturethe yellow solution was cooled to rt
  3. washthe organic layer was washed successively with 1 N HCl and brine
  4. dry with materialAfter drying over Na2SO4
  5. concentrationconcentrating
  6. customthe pale yellow solid was purified twice by silica gel chromatography (DCM:MeOH 100:6 and DCM:MeOH 100:5)

Sources & evidence

ORD record
ord-034b1b6c59c84127a9b1691b0cd3dd34
Source dataset
uspto-grants-2007_10
Patent number
US07285671B2

Reaction notes

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