Water → HCID 21072945, compound

HRID 1373215Notes

Reaction equation

HRID 1373215 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)=[C:6]([CH:23]=1)[O:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C([CH:36]([CH2:40][C:41](Cl)=[O:42])[C:37](Cl)=[O:38])C.O1CC[CH2:46][CH2:45]1.[OH2:49]>CN(C)C1C=CN=CC=1>[C:15]([O:14][C:13]([NH:12][CH2:11][C:10]1[CH:9]=[C:8]([CH:22]=[CH:21][CH:20]=1)[O:7][C:6]1[CH:23]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N:24]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=1)[C:41](=[O:42])[CH2:40][CH2:36][C:37]([O:38][CH2:45][CH3:46])=[O:49])=[O:19])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 21073110HCID 21073110, compoundHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 21072945HCID 21072945, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of tert-butyl 3-[5-chloro-2-(3,4-dichlorobenzylamino)phenoxy]benzylcarbamate (2.79 g, 5.5 mmols), ethylsuccinyl chloride (1.2 ml, 8.3 mmols), 4-dimethylaminopyridine (1.01 g, 8.3 mmols) and tetrahydrofuran (30 ml) was stirred at room temperature for 1 hour, and then at 60° C. for 3 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with brine, 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 oil of ethyl N-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]-N-(3,4-dichlorobenzyl)succinamate (3.34 g, 95.7%).

Workup

  1. waitat 60° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThis was concentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-3a30f2cdd6914f7cb2a3311d95dfc0b7
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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