Water → HCID 5296614, compound

HRID 1371535Notes

Reaction equation

HRID 1371535 reaction equation
Cl.[NH2:2][CH:3]([C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=1)[CH2:4][C:5]([OH:7])=[O:6].O.[C:18]1([CH2:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[C:18]1([CH2:24][C:25]([NH:2][CH:3]([C:8]2[CH:16]=[CH:15][C:11]3[O:12][CH2:13][O:14][C:10]=3[CH:9]=2)[CH2:4][C:5]([OH:7])=[O:6])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 46735907HCID 46735907, compound

Product 1

HCID 5296614HCID 5296614, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
-5 °C

Procedure

20 g of 3-amino-3-(benzo[1,3]dioxol-5-yl)propionic acid hydrochloride are placed in 10 ml of acetone, 30 ml of water and 38 ml of TEA at −5° C. and 14 ml of phenylacetyl chloride in 20 ml of acetone are added dropwise, followed by stirring for 2 hours at −5° C. The acetone is concentrated. The aqueous phase is washed with Et2O and the insoluble material is removed by filtration. The phases are separated again by settling and the aqueous phase is washed with Et2O and then acidified with 1N HCl to pH 2. The resulting phase is poured into DCM and a precipitate forms. The precipitate is filtered off by suction and rinsed with DCM. 24 g of the expected compound are obtained.

Workup

  1. concentrationThe acetone is concentrated
  2. washThe aqueous phase is washed with Et2O
  3. customthe insoluble material is removed by filtration
  4. customThe phases are separated again
  5. washthe aqueous phase is washed with Et2O
  6. additionThe resulting phase is poured into DCM
  7. filtrationThe precipitate is filtered off by suction
  8. washrinsed with DCM

Sources & evidence

ORD record
ord-81f2708a7cbc4e989e4a9c5a283efb48
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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