Hydrochloric Acid → HCID 21021994, compound

HRID 1794223Notes

Reaction equation

HRID 1794223 reaction equation
C([O:3][C:4]([C@@H:6]1[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][C@H:17]([NH:19][CH2:20][C@H:21]([OH:39])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([O:30]COC)=[C:26]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:25]=3)[CH3:18])=[CH:15][C:9]=2[O:8][CH2:7]1)=[O:5])C.Cl>>[OH:39][C@H:21]([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([NH:34][S:35]([CH3:38])(=[O:36])=[O:37])[CH:25]=1)[CH2:20][NH:19][C@H:17]([CH3:18])[CH2:16][C:14]1[CH:13]=[CH:12][C:10]2[O:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7][O:8][C:9]=2[CH:15]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58618722HCID 58618722, compound

Product 1

HCID 21021994HCID 21021994, compoundYield 62%

Procedure

A solution of 6-[2-(R)-[2-(S)-hydroxy-3-[3-methanesulfonamido-4-(methoxymethoxy)phenoxy]propylamino]propyl]-2,3-dihydro-1,4-benzodioxine-2-(R)-carboxylic acid ethyl ester (220 mg) obtained in Example 1 in 1N—HCl (9 mL) was stirred under reflux for 3 hours. After allowing to cool to room temperature, it was concentrated to dryness under reduced pressure. The residue was dissolved in water/acetonitrile=1/1(v/v) (10 mL) and the pH was adjusted to 6.0 by addition of saturated aqueous sodium bicarbonate. After concentrating under reduced pressure, the residue was purified by HP column chromatography and the title compound was obtained from the effluent with water/methanol=50/50 (v/v). Yield: 62%

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationit was concentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in water/acetonitrile=1/1(v/v) (10 mL)
  4. additionthe pH was adjusted to 6.0 by addition of saturated aqueous sodium bicarbonate
  5. concentrationAfter concentrating under reduced pressure
  6. customthe residue was purified by HP column chromatography

Sources & evidence

ORD record
ord-c789bcea465c4c799ef8fc3dc953e3a2
Source dataset
uspto-grants-2006_04
Patent number
US07022732B2

Reaction notes

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