Water → 220129-58-8

HRID 843316Notes

Reaction equation

HRID 843316 reaction equation
P(O)(O)(O)=O.[OH:6][C@H:7]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[C@@H:8]([NH:10][CH2:11][CH2:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=1)[CH3:9].[OH-].[Na+].P(=O)(O)(O)O.O>CO>[OH:6][C@H:7]([C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)[C@@H:8]([NH:10][CH2:11][CH2:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1)[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 69757681HCID 69757681, compound

Product 1

HCID 9798256220129-58-8Yield 110.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To ethyl 2-[4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxy-phenyl)-1-methylethyl]amino]ethyl]phenoxy]acetate phosphate (62.0 g) was added 2 mole/L aqueous sodium hydroxide solution (393 mL), and the mixture was heated to 40° C. of internal temperature with stirring to dissolve. 4 Mole/L aqueous phosphoric acid solution (115 mL) was added dropwise to the solution at 40-46° C. of internal temperature. After stirring at room temperature overnight, the resulting crystals were collected by filtration and washed with water to obtain white crystals. The resulting crystals suspended in a mixed solvent (200 mL) of water and methanol (1/8) were heated under reflux for 30 minutes. After cooling to room temperature, the crystals were collected by filtration and dried at 40-50° C. for 3 hours under reduced pressure to give 2-[4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]acetic Acid (Crystalline Form α) (50.0 g). A powder X-ray diffraction pattern of the crystalline polymorph (crystalline form α) is shown in the following FIG. 1.

Workup

  1. dissolutionto dissolve
  2. stirringAfter stirring at room temperature overnight
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with water
  5. customto obtain white crystals
  6. temperaturewere heated
  7. temperatureunder reflux for 30 minutes
  8. temperatureAfter cooling to room temperature
  9. filtrationthe crystals were collected by filtration
  10. customdried at 40-50° C. for 3 hours under reduced pressure

Sources & evidence

ORD record
ord-ba8f542cc8994d80b976975f6444f04a
Source dataset
uspto-grants-2002_04
Patent number
US06376707B1

Reaction notes

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