Triethylamine → benzyl (3R)-4-(5-cyano-2-iodophenoxy)-3-(4-cyanobenzoylamino)butanoate

HRID 747768Notes

Reaction equation

HRID 747768 reaction equation
[Cl-].[CH2:2]([O:9][C:10]([CH2:12][C@@H:13]([NH3+:25])[CH2:14][O:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:17]=1[I:24])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:26]([C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1)#[N:27].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl.O>[C:22]([C:20]1[CH:19]=[CH:18][C:17]([I:24])=[C:16]([CH:21]=1)[O:15][CH2:14][C@H:13]([NH:25][C:32](=[O:33])[C:31]1[CH:35]=[CH:36][C:28]([C:26]#[N:27])=[CH:29][CH:30]=1)[CH2:12][C:10]([O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:11])#[N:23]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 120874-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86760714(1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethylammonium chloride

Product 1

HCID 54164296benzyl (3R)-4-(5-cyano-2-iodophenoxy)-3-(4-cyanobenzoylamino)butanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

4.73 g (10 mmol) of (1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethylammonium chloride, 2.9 g (20 mmol) of 4-cyanobenzoic acid, 3.0 g (22 mmol) of 1-hydroxybenzotriazole and 6.1 ml (44 mmol) of triethylamine were dissolved in 50 ml of dichloromethane. 4.2 g (22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to the solution under cooling with ice, and they were stirred for 10 minutes and then at room temperature for one hour. Water is added to the reaction mixture to terminate the reaction. The mixture was treated with dichloromethane as the extractant in an ordinary manner to obtain the crude product, which was purified by the silica gel column chromatography (volume ratio of hexane:ethyl acetate=3:1) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. waitat room temperature for one hour
  3. customto terminate
  4. customthe reaction
  5. customto obtain the crude product, which
  6. customwas purified by the silica gel column chromatography (volume ratio of hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0ce0e02527c842c7999849f0faed2d91
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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