Water → HCID 69352570, compound

HRID 1373211Notes

Reaction equation

HRID 1373211 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])=[CH:27][CH:26]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([CH:42]([CH2:46][C:47](Cl)=[O:48])[C:43](Cl)=[O:44])C.O1CC[CH2:52][CH2:51]1.[OH2:55]>CN(C)C1C=CN=CC=1>[Si:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:23]([C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[O:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:39])[CH:10]=2)[C:47](=[O:48])[CH2:46][CH2:42][C:43]([O:44][CH2:51][CH3:52])=[O:55])=[CH:26][CH:27]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 21073106HCID 21073106, compoundHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 69352570HCID 69352570, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of tert-butyl[3-[2-(4-tert-butyldimethylsilyloxybenzylamino)-5-chlorophenoxy]benzyl]carbamate (2.58 g, 5 mmols), ethylsuccinyl chloride (1.1 ml, 7.5 mmols), 4-dimethylaminopyridine (0.92 g, 7.5 mmols) and tetrahydrofuran (30 ml) was stirred at room temperature 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-(4-tert-butyldimethylsilyloxybenzyl)-N-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]succinamate (2.18 g, 31.3%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  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-1e63000f90ba4fccb8858d0c7239124a
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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