Bicarbonate Ion → HCID 67247376, compound

HRID 2425327Notes

Reaction equation

HRID 2425327 reaction equation
[OH:1][CH2:2][C:3]([NH:25][C:26](=[O:28])[CH3:27])([CH2:23][OH:24])[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:12]=2)[CH2:7][CH:6]1O.C1(C)C(S(O)(=O)=O)=CC=CC=1.O.C(=O)(O)[O-]>C1(C)C=CC=CC=1>[OH:24][CH2:23][C:3]([NH:25][C:26](=[O:28])[CH3:27])([CH2:2][OH:1])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:12]=2)[CH2:7][CH:6]=1

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 962WaterHCID 69252-Methylbenzenesulfonic acidHCID 67247921HCID 67247921, compound

Product 1

HCID 67247376HCID 67247376, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 18 (85 mg, 022 mmol) is dissolved in toluene (10 mL), toluenesulphonic acid (˜5 mg) is added, and the reaction heated to reflux for 3 hours with continuous removal of water from the condensed azeotrope. The reaction is cooled, then poured into aqueous bicarbonate (5% w/w, 10 mL) and the aqueous layer extracted with ether (5 mL) twice. The organic layers are combined and removed in vacuo to provide the crude residue that upon silica gel chromatography provide 19.

Workup

  1. temperaturethe reaction heated
  2. temperatureThe reaction is cooled
  3. extractionthe aqueous layer extracted with ether (5 mL) twice
  4. customremoved in vacuo
  5. customto provide the crude residue that upon silica gel chromatography

Sources & evidence

ORD record
ord-abcf591144554cd2a685a56852ea1d5a
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

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