Toluene → HCID 12040974, compound

HRID 1837827Notes

Reaction equation

HRID 1837827 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.[C:24]1(C)[CH:29]=CC=C[CH:25]=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][C:24]1([CH3:29])[CH3:25])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 15198452HCID 15198452, compound

Product 1

HCID 12040974HCID 12040974, compoundYield 93%

Procedure

[R-(R*,S*)]-β-(Benzoylamino)-α-hydroxybenzenepropanoic acid, ethyl ester (2.200 mg) was suspended in toluene (250 ml) and the flask equipped with a Dean-Stark trap. After heating to reflux, the compound dissolved. 40 ml of toluene were distilled off, PPTS (120 mg) and 2-methoxypropene (3.5 ml) were added, and distillation was continued. Further additions of 2-methoxypropene (2 ml, and then 1 ml) and toluene (50 ml, and then another 50 ml) were made, and the distillate periodically discarded. Purification on HPLC (hexane/ethyl acetate, 3:1) gave 2.3 g (93%) of the title product in a mixture with other reaction products. (Product characteristics consistent with structure of Example 1.)

Workup

  1. customthe flask equipped with a Dean-Stark trap
  2. temperatureAfter heating
  3. temperatureto reflux
  4. dissolutionthe compound dissolved
  5. distillation40 ml of toluene were distilled off
  6. additionPPTS (120 mg) and 2-methoxypropene (3.5 ml) were added
  7. distillationdistillation
  8. customPurification on HPLC (hexane/ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-cec17a45c01b4b76a7024fcac703f8d3
Source dataset
uspto-grants-2004_08
Patent number
US06784304B2

Reaction notes

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