(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate → HCID 68433068, compound

HRID 1867434Notes

Reaction equation

HRID 1867434 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].CC([O-])(C)C.[K+].[CH3:27][C:28]1([CH3:45])[O:32][C@H:31]([CH2:33]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:30][O:29]1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:33][C@@H:31]3[CH2:30][O:29][C:28]([CH3:45])([CH3:27])[O:32]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 2723760(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-ToluenesulfonateHCID 23665647Potassium tert-butoxideHCID 620449211-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one2×

Product 1

HCID 68433068HCID 68433068, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.26 g (20.00 mmol) of 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one (intermediate 1A]) in 200 ml of THF was treated at 0° C. with 2.47 g (22.00 mmol) of potassium tert-butylate and after 10 min with 5.73 (20.00 mmol) of toluene-4-sulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester. The reaction was stirred for 14 h at RT, 28 h at reflux temperature, cooled and extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (CH2Cl2/MeOH 97.5/2.5) to yield 4.27 g (50%) of the title compound as off-white powder. MS: 427.1 (MH+, 2Cl).

Workup

  1. temperatureat reflux temperature
  2. temperaturecooled
  3. extractionextracted with aqueous saturated NaHCO3/Et2O (3×)
  4. washThe organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. custompurified by flash silica gel column (CH2Cl2/MeOH 97.5/2.5)

Sources & evidence

ORD record
ord-49ff0f4ac72547d7a8ad7f15a80fd4fb
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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