Acetic Acid → HCID 59714902, compound

HRID 2223847Notes

Reaction equation

HRID 2223847 reaction equation
[NH2:1][C:2]([CH2:7][OH:8])([CH2:5][OH:6])[CH2:3][OH:4].Cl.C([O:12][CH2:13][CH3:14])C.[C:15](OC(=O)C)(=[O:17])[CH3:16].[C:22](O)(=[O:24])[CH3:23]>>[C:15]([O:4][CH2:3][C:2]([NH2:1])([CH2:7][O:8][C:13](=[O:12])[CH3:14])[CH2:5][O:6][C:22](=[O:24])[CH3:23])(=[O:17])[CH3:16]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6503Tris(hydroxymethyl)aminomethaneHCID 7918Acetic AnhydrideHCID 10953452Ether hydrochloride

Product 1

HCID 59714902HCID 59714902, compound

Conditions

Temperature
110 °C

Procedure

To 2-amino-2-hydroxymethyl-1,3-propanediol (10.00 g) were added acetic acid (40.0 mL), 1N hydrochloric acid/diethyl ether solution (90.0 mL) and acetic anhydride (30.0 mL) successively. The solution was heated under reflux at 110° C. for 6 hours. The solvent was distilled off under reduced pressure, and distilled to dryness with xylene azeotropically. The resulting residue was diluted with water, washed with ethyl acetate, the aqueous layer was made to pH 8 with sodium hydrogencarbonate, and it was then extracted with 25% ethanol/chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel, 3-4% ethanol/dichloromethane) to give the title compound (4.02 g).

Workup

  1. temperatureThe solution was heated
  2. distillationThe solvent was distilled off under reduced pressure
  3. distillationdistilled to dryness with xylene azeotropically
  4. additionThe resulting residue was diluted with water
  5. washwashed with ethyl acetate
  6. extractionwas then extracted with 25% ethanol/chloroform
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by column chromatography (silica gel, 3-4% ethanol/dichloromethane)

Sources & evidence

ORD record
ord-28bd7fca47164c0b8e2ef7728cba50ef
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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