Ethyl Acetate → HCID 59540987, compound

HRID 1677469Notes

Reaction equation

HRID 1677469 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:6][O:7][Si:8]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:9]([CH3:11])[CH3:10])[C:3]([OH:5])=O.CCN=C=NCCCN(C)C.Cl.[CH3:31][NH:32][O:33][CH3:34].CCOC(C)=O>ClCCl.CN(C1C=CN=CC=1)C>[CH3:34][O:33][N:32]([CH3:31])[C:3](=[O:5])[C:2]([CH3:1])([CH3:18])[CH2:6][O:7][Si:8]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:9]([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 59541078HCID 59541078, compound

Product 1

HCID 59540987HCID 59540987, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2-dimethyl-3-triisopropylsilanyloxy-propionic acid in anhydrous dichloromethane (13 ml) was slowly treated with EDCI (1.03 g, 5.38 mmol) followed by N,O -dimethylhydroxylamine hydrochloride (525 mg, 5.4 mmol), DMAP (55 mg, 0.045 mmol), and TEA (0.75 ml, 5.38 mmol). After stirring overnight at room temperature the reaction mixture was partitioned between DCM/water. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a greenish oil. Silica gel chromatography using 10-60% EtOAc in hexanes as eluant provided 1.13 mg (79%) of N-methoxy-2,2,N-trimethyl-3-triisopropylsilanyloxy-propionamide as a colorless oil. M+H=318.

Workup

  1. customwas partitioned between DCM/water
  2. customThe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customgiving a greenish oil

Sources & evidence

ORD record
ord-cd3f675bcde34f6aab386c32ca856882
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

Loading…