Triethylamine → HCID 67332870, compound

HRID 1988075Notes

Reaction equation

HRID 1988075 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH:6]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:12])[C:7]([OH:9])=O.CCN=C=NCCCN(C)C.[NH2:37][CH2:38][CH2:39][CH2:40][CH2:41][OH:42].CCN(CC)CC>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH:6]([NH:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:17][CH:18]=1)=[O:12])[C:7](=[O:9])[NH:37][CH2:38][CH2:39][CH2:40][CH2:41][OH:42]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 258684-Amino-1-butanolHCID 45496562HCID 45496562, compound

Product 1

HCID 67332870HCID 67332870, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[(Biphenyl-4-carbonyl)-amino]-pentanedioic acid 5-methyl ester (400 mg, 1.2 mmol, 1 equiv.) in DMF (10 mL) was added to EDCI (337 mg, 1.8 mmol, 1.5 equiv.). The solution was stirred at room temperature under N2 for 40 min. 4-Amino-1-butanol (0.11 mL, 1.2 mmol, 1 equiv.) was added, followed by addition of Et3N (0.41 mL, 2.9 mmol, 2.5 equiv.) and DMAP (72 mg, 0.59 mmol, 0.5 equiv.). The mixture was stirred overnight under N2. The reaction mixture was then poured into cold water and a solid precipitated from the solution. The solid was collected by filtration and dried under vacuum to give 229 mg of 4-[(Biphenyl-4-carbonyl)-amino]-4-(4-hydroxy-butylcarbamoyl)-butyric acid methyl ester in 47% yield.

Workup

  1. stirringThe mixture was stirred overnight under N2
  2. customa solid precipitated from the solution
  3. filtrationThe solid was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ae57a770f7c640be8d7726c5911fbfca
Source dataset
uspto-grants-2009_06
Patent number
US07553873B2

Reaction notes

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