Dimethylformamide → HCID 59918716, compound

HRID 840351Notes

Reaction equation

HRID 840351 reaction equation
[C:1]([NH:9][CH:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:11]([OH:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][CH:26](OC)OC.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.CN(C=O)C>C1C=CC=CC=1>[C:1]([N:9]1[C@@H:10]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:17][CH:24]1[O:25][CH3:26])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9005Trimethyl orthoformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 15198452HCID 15198452, compound

Product 1

HCID 59918716HCID 59918716, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
103 °C

Procedure

[R-(R*,S*)]-β-(Benzoylamino)-α-hydroxybenzenepropanoic acid, ethyl ester (1.16 mmol) was suspended in benzene (10 ml), and trimethoxymethane (3.44 mmol) and PPTS (72 mg) were added. Heating to reflux (103° C.) did not dissolve the starting compound. 2 ml of DMF were then added so that most of the starting compound dissolved, although the solution remained somewhat turbid. The flask was equipped with a Soxhlet extractor. The thimble of the extractor was filled with 4 Å mol. sieves. After 1 hour, and approximately 3 to 4 cycles in the Soxhlet extractor, TLC showed consumption of the starting material, and a new major spot of the title product. It was diluted with EtOAc, washed with NaHCO3 and H2O, dried and the solvent removed. NMR showed the presence of the title product and a small impurity. The product was purified on HPLC (hexane:ethyl acetate, 3:1) to give 358 mg (87%) of the title product.

Workup

  1. temperatureHeating
  2. dissolutiondid not dissolve the starting compound
  3. dissolutiondissolved, although the solution
  4. customThe flask was equipped with a Soxhlet extractor
  5. additionThe thimble of the extractor was filled with 4 Å mol
  6. customconsumption of the starting material
  7. additionIt was diluted with EtOAc
  8. washwashed with NaHCO3 and H2O
  9. customdried
  10. customthe solvent removed
  11. customThe product was purified on HPLC (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-2582670b3bab4536b4a8ca0298111f12
Source dataset
uspto-grants-2002_04
Patent number
US06365750B1

Reaction notes

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