Dichloromethane → HCID 20312443, compound

HRID 1731048Notes

Reaction equation

HRID 1731048 reaction equation
[CH2:1]([O:5][C:6](=[O:23])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH2:2][CH2:3][CH3:4].[C:24]1([S:30][CH3:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)Cl>B(F)(F)F.CCOCC.CCCCCC>[CH2:1]([O:5][C:6](=[O:23])[CH:7]([C:27]1[CH:28]=[CH:29][C:24]([S:30][CH3:31])=[CH:25][CH:26]=1)[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 7520ThioanisoleHCID 20312421HCID 20312421, compound

Product 1

HCID 20312443HCID 20312443, compound

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 8058HexaneSolvent

Procedure

A solution of 1.6 g. (5.0 mmol.) of N-benzyloxycarbonyl-2-acetoxyglycine n-butyl ester, 1.0 g. (8.0 mmol.) of thioanisole and 10 drops of boron trifluoride etherate in 10 ml. of methylene chloride was stirred at 25° for 2 hours. The reaction mixture was diluted with hexane and chromatographed on silica gel with hexane followed by 1:1 chloroform-hexane to give the title compound.

Workup

  1. customchromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-bb6f209d0af24119b92ca42647f20023
Source dataset
uspto-grants-1976_11
Patent number
US03994954

Reaction notes

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