Triethylamine → tert-Butyl 7-(4-(allyloxy)phenyl)-5-oxo-9-oxa-2-thia-4,8-diazaundec-7-en-3-ylidenecarbamate

HRID 2243868Notes

Reaction equation

HRID 2243868 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:16][O:17][CH2:18][CH3:19])[CH2:12][C:13]([OH:15])=O)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[NH2:20][C:21](=[N:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[S:22][CH3:23].C(N(CC)CC)C>ClCCl>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[N:16][O:17][CH2:18][CH3:19])[CH2:12][C:13](=[O:15])[NH:20][C:21](=[N:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[S:22][CH3:23])=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 54237411CarbaMic acid, [iMino(Methylthio)Methyl]-, 1,1-diMethylethyl ester (9CI)HCID 725319043-(4-(Allyloxy)phenyl)-3-(ethoxyimino)propanoic acid

Product 1

HCID 72531903tert-Butyl 7-(4-(allyloxy)phenyl)-5-oxo-9-oxa-2-thia-4,8-diazaundec-7-en-3-ylidenecarbamateYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-(Allyloxy)phenyl)-3-(ethoxyimino)propanoic acid from Step C (850 mg), tert-butyl amino(methylthio)methylenecarbamate (675 mg), Py.Bop (2.01 g), and triethylamine (0.68 mL) in dichloromethane (1.8 mL) was stirred at room temperature for 12 h. The crude reaction mixture was purified directly by Boitage flash chromatography eluting with 15-30% ethyl acetate/85-70% hexanes to give the title compound as a white solid (1.14 g). HPLC retention time: 2.37 min (method A). MS (ESI) (M+Na)+ 436.25.

Workup

  1. customThe crude reaction mixture
  2. customwas purified directly by Boitage flash chromatography
  3. washeluting with 15-30% ethyl acetate/85-70% hexanes

Sources & evidence

ORD record
ord-aa8c2041131e460aa9e8d4ecde1c7924
Source dataset
uspto-grants-2010_03
Patent number
US07678784B2

Reaction notes

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