1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68525625, compound

HRID 2247657Notes

Reaction equation

HRID 2247657 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[Si]([O:45][CH2:46][C:47]1[S:51][CH:50]=[C:49]([C:52](=[N:54]O)[NH2:53])[CH:48]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:12]2[O:14][N:54]=[C:52]([C:49]3[CH:48]=[C:47]([CH2:46][OH:45])[S:51][CH:50]=3)[N:53]=2)=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1364294-Benzylbenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 866202125-({[t-Butyl(dimethyl)silyl]oxy}methyl)-N'-hydroxythiophene-3-carboximidamide

Product 1

HCID 68525625HCID 68525625, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 5 (5a) using 4-benzylbenzoic acid (0.12 g, 0.55 mmol), 1-hydroxybenzotriazole (88 mg, 0.65 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.12 g, 0.60 mmol), 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxythiophene-3-carboximidamide (0.14 g, 0.5 mmol) that was obtained in Example 3 (3b), and tetrabutylammonium fluoride (a 1.0 M solution in tetrahydrofuran, 1.0 ml, 1.0 mmol). Subsequently, the crude product of the title compound thus obtained was purified by recrystallization from a mixed solvent of ethyl acetate and hexane to afford the title compound (99 mg) in a yield of 57% as a white crystalline solid.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-867631a6356d41708209a49ea0a73364
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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