Benzenepentanoic acid → HCID 59924200, compound

HRID 2298749Notes

Reaction equation

HRID 2298749 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.[NH2:36][C@H:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:38][OH:39]>CN(C=O)C.O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([NH:36][C@H:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:38][OH:39])=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 16757Benzenepentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724025(R)-beta-aminophenethyl alcoholHCID 178418300HCID 178418300, compound

Product 1

HCID 59924200HCID 59924200, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-phenylpentanoic acid (1.25 g) and hydroxybenzotriazole (1.18 g) in N,N′-dimethylformamide (25 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.74 g) at 0° C. and the mixture was stirred for 1 hour. To the mixture was added (2R)-2-amino-2-phenylethanol (960 mg) and the mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into water (150 ml) and then extracted with ethyl acetate. The organic layer was washed with 2N hydrochloric acid, 2N aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystal was washed with diethy ether to give the title compound (1.09 g) having the following physical data.

Workup

  1. stirringthe mixture was stirred for 2 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 2N hydrochloric acid, 2N aqueous solution of sodium hydroxide
  4. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe obtained crystal was washed with diethy ether

Sources & evidence

ORD record
ord-0b1decffa4d8440a874b69c8695b7efe
Source dataset
uspto-grants-2002_12
Patent number
US06495533B1

Reaction notes

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