Isopropanol → Ornithine phenylacetate

HRID 1844762Notes

Reaction equation

HRID 1844762 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][CH2:13][CH2:14][NH2:15].C(OC1C=CC=CC=1)(=O)C.[Na].CC(O)C>O>[C:2]1([CH2:1][C:16]([OH:18])=[O:17])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][CH2:13][CH2:14][NH2:15]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 66717857HCID 66717857, compound2×HCID 66718093HCID 66718093, compound2×

Product 1

HCID 44247677Ornithine phenylacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
4 °C

Procedure

7.6 g (0.03 moles) of the L-ornithine benzoate was dissolved in 38 mL H2O and about 4.4 g of sodium phenyl acetate was dissolved 22 mL H2O, Subsequently, the sodium phenyl acetate solution was added to the L-ornithine benzoate solution and left to stir for about 10 minutes. About 240 mL of IPA (8:2 IPA:H2O) was added and the solution stirred for 30 minutes before cooling to 4° C. A crystalline solid precipitated after about 3 hours at 4° C. (L-ornithine phenyl acetate). The precipitate was isolated by vacuum filtration and washed with 48-144 mL of IPA. Yield: 57%.

Workup

  1. waitleft
  2. stirringthe solution stirred for 30 minutes
  3. customA crystalline solid precipitated after about 3 hours at 4° C. (L-ornithine phenyl acetate)
  4. customThe precipitate was isolated by vacuum filtration
  5. washwashed with 48-144 mL of IPA

Sources & evidence

ORD record
ord-74fa6123cc2145899ca73475f8030707
Source dataset
uspto-grants-2015_02
Patent number
US08946473B2

Reaction notes

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