1-Hydroxybenzotriazole → HCID 69621010, compound

HRID 566417Notes

Reaction equation

HRID 566417 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[ClH:17].[CH2:18]([O:20][C:21](=[O:31])[C@H:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:23])[CH3:19].CCN=C=N[CH2:37][CH2:38][CH2:39][N:40]([CH3:42])C.Cl.[CH:44]1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(N(CC)CC)C>[ClH:17].[CH2:18]([O:20][C:21](=[O:31])[C@H:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:23][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:44][CH2:37][CH2:38][CH2:39][NH:40][CH3:42])=[CH:7][CH:6]=2)=[CH:16][CH:15]=1)[CH3:19]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 69621010HCID 69621010, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(4-hydroxyphenyl)benzoic acid (3.0 g) and L-phenylalanine ethyl ester hydrochloride (3.38 g) in DMF (30 ml) were added WSC.HCl (2.7 g), HOBT (1.89 g) and triethylamine (2 ml), and the mixture was stirred at room temperature for 14 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a 10% aqueous citric acid solution, water, a saturated aqueous sodium hydrogen-carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with a 10% aqueous citric acid solution, water
  3. dry with materiala saturated aqueous sodium hydrogen-carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a1d5eca8d504cf68a2c7d496a7f891f
Source dataset
uspto-grants-2001_01
Patent number
US06174887B1

Reaction notes

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