Dimethylformamide → HCID 59918716, compound

HRID 840352Notes

Reaction equation

HRID 840352 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 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Preparation of the title compound was conducted on a larger scale as follows. [R-(R*,S*)]-β-(Benzoylamino)-α-hydroxybenzenepropanoic acid, ethyl ester (3.138 g) was suspended in benzene (100 ml), and trimethoxymethane (3.190 g) and PPTS (628 mg) were added. The reaction solution was heated to reflux, 20 ml of DMF were added for dissolution of most of the starting compound, followed by heating with a Soxhlet extractor. The thimble in 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 3.138 g (97%) of the title product. The product (an oil) was a mixture of diastereomers (not separated). Mass spec.: M+H+=356

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux
  3. temperatureby heating with a Soxhlet extractor
  4. additionThe thimble in the extractor was filled with 4 Å mol
  5. customconsumption of the starting material
  6. additionIt was diluted with EtOAc
  7. washwashed with NaHCO3 and H2O
  8. customdried
  9. customthe solvent removed
  10. customThe product was purified on HPLC (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-528bb5f0cdd14d93bbe13205ee61d5d6
Source dataset
uspto-grants-2002_04
Patent number
US06365750B1

Reaction notes

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