Triethylamine → HCID 178472005, compound

HRID 963425Notes

Reaction equation

HRID 963425 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8](=[CH:14]N(C)C)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([Cl:20])[CH:3]=1.[NH2:21][C:22]([CH3:26])([CH3:25])[CH2:23][OH:24].C(N(CC)CC)C.[C:34]([Si:38]([CH3:41])([CH3:40])Cl)([CH3:37])([CH3:36])[CH3:35]>ClCCCl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8](=[CH:14][NH:21][C:22]([CH3:26])([CH3:25])[CH2:23][O:24][Si:38]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:41])[CH3:40])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([Cl:20])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 54513699HCID 54513699, compound

Product 1

HCID 178472005HCID 178472005, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

3.6 g of ethyl 2-(4-bromo-2-chloro-benzoyl)-3-dimethylaminoacrylate (Example 13bk)) and 2-amino-2-methyl-1-propanol in 40 ml of 1,2-dichloroethane were stirred at room temperature for 1 hr. with the direct introduction of argon. Then, 0.74 ml of triethylamine, 1.66 g of tert.-butyldimethylchlorosilane and 1.22 mg of 4-dimethylaminopyridine were added and the mixture was stirred at room temperature for 24 hrs. The reaction mixture was chromatographed directly on silica gel in dichloromethane. 4.64 g (92%) of ethyl 2-(4-bromo-2-chloro-benzoyl)-3-[2-(tert.-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethylamino]-acrylate were obtained as a colourless oil. Mass spectrum (ISP): peaks inter alia at 520 (M+H, 100%), 518 (75%).

Workup

  1. customwere stirred at room temperature for 1 hr
  2. customThe reaction mixture was chromatographed directly on silica gel in dichloromethane

Sources & evidence

ORD record
ord-dc5756ae98c0425bbbc21bf2305d9a1f
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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