Tetrahydrofuran → (6R)-6-(5-chloro-2-methoxybenzyl)-2-thioxo-1-(2,4,6-trimethoxybenzyl)-1,4-diazepan-5-one

HRID 80586Notes

Reaction equation

HRID 80586 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([CH:30]=1)[CH2:7][C@@H:8]1[CH2:14][N:13]([CH2:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][C:17]=2[O:26][CH3:27])[C:12](=O)[CH2:11][NH:10][C:9]1=[O:29].O1CCCC1.C1C=CC(OC2C=CC(P3(SP(C4C=CC(OC5C=CC=CC=5)=CC=4)(=S)S3)=[S:52])=CC=2)=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([CH:30]=1)[CH2:7][C@@H:8]1[CH2:14][N:13]([CH2:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][C:17]=2[O:26][CH3:27])[C:12](=[S:52])[CH2:11][NH:10][C:9]1=[O:29]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 118134142,4-Bis(4-phenoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetaneHCID 66934888HCID 66934888, compound

Product 1

HCID 88994535(6R)-6-(5-chloro-2-methoxybenzyl)-2-thioxo-1-(2,4,6-trimethoxybenzyl)-1,4-diazepan-5-oneYield 124.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the compound S140c described in WO 06-059801A, that is, (6R)-6-(5-chloro-2-methoxybenzyl)-1-(2,4,6-trimethoxybenzyl)-1,4-diazepane-2,5-dione (2.2 g) in a tetrahydrofuran (80 ml) solution, Belleau's reagent (1.5 g) was added under ice cooling, and the mixture was stirred at that temperature for 3 hours. The reaction solution was diluted with ethyl acetate, successively washed with saturated aqueous sodium hydrogencarbonate solution, water, and brine, dried over anhydrous sodium sulfate, then concentrated. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=35/65 to 1/99) to obtain the title compound (1.69 g).

Workup

  1. washsuccessively washed with saturated aqueous sodium hydrogencarbonate solution, water, and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=35/65 to 1/99)

Sources & evidence

ORD record
ord-729a710c22c244f282dbc5ea8410b665
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Reaction notes

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