Triethylamine → HCID 21073054, compound

HRID 1373213Notes

Reaction equation

HRID 1373213 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][CH:39]=1)[O:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N:21]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1)[C:22](=[O:28])[CH2:23][CH2:24][C:25]([OH:27])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:40][C:41]1[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=1[CH2:43][NH2:44].P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>O.CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][CH:39]=1)[O:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N:21]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=1)[C:22](=[O:28])[CH2:23][CH2:24][C:25]([NH:44][CH2:43][C:42]1[CH:45]=[CH:46][CH:47]=[CH:48][C:41]=1[F:40])=[O:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 666492-FluorobenzylamineHCID 76257Diethyl cyanophosphonateHCID 21073055HCID 21073055, compound

Product 1

HCID 21073054HCID 21073054, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]-N-(4-hydroxybenzyl)succinamic acid (0.67 g, 1.2 mmols), 2-fluorobenzylamine (0.16 ml, 1.4 mmols), diethyl cyanophosphate (0.20 ml, 1.4 mmols), triethylamine (0.20 ml, 1.4 mmols) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give an amorphous solid of N-[2-[3(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]-N-(4-hydroxybenzyl)-N′-(2-fluorobenzyl)succinamide (0.69 g, 97%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationThis was concentrated under reduced pressure
  5. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-9b4a1c72dfbe46439d048e32ed0cd6e0
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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