Chlorotrimethylsilane → 3-{5-(tert-Butyl-dimethyl-silanyloxy)-2-[(4-methoxy-phenyl)-(4-nitro-phenylamino)-methyl]-5-phenyl-pentanoyl}-4-phenyl-oxazolidin-2-on

HRID 2115188Notes

Reaction equation

HRID 2115188 reaction equation
[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][CH:7]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:8][CH2:9][CH2:10][C:11]([N:13]1[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][O:15][C:14]1=[O:24])=[O:12])([CH3:4])([CH3:3])[CH3:2].[CH3:33][O:34][C:35]1[CH:51]=[CH:50][C:38]([CH:39]=[N:40][C:41]2[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=2)=[CH:37][CH:36]=1.C(N(C(C)C)CC)(C)C.C[Si](Cl)(C)C.S([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)(=O)C>[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][CH:7]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:8][CH2:9][CH:10]([CH:39]([C:38]1[CH:50]=[CH:51][C:35]([O:34][CH3:33])=[CH:36][CH:37]=1)[NH:40][C:41]1[CH:42]=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45][CH:46]=1)[C:11]([N:13]1[CH:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][O:15][C:14]1=[O:24])=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 81531DiisopropylethylamineHCID 262174N-(p-Methoxybenzylidene)-p-nitroanilineHCID 210831813-[5-(tert-Butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyl]-4-phenyl-oxazolidin-2-onHCID 23665763Sodium Bisulfite

Product 1

HCID 686400833-{5-(tert-Butyl-dimethyl-silanyloxy)-2-[(4-methoxy-phenyl)-(4-nitro-phenylamino)-methyl]-5-phenyl-pentanoyl}-4-phenyl-oxazolidin-2-onYield 74%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

To 5.4 g (12.0 mmol) of product 1 and 6.2 g (24 mmol) of product 2 in 135 ml of methylenchloride 8 ml of diisopropylethylamin is added at 10° C. and 4.8 ml of trimethylsilylchloride is added dropwise. After 1 h 14 ml of a 1 molar solution of titantetrachloride in methylenchloride is added dropwise at —10° C. It is stirred for 3 h at −10° C. and further 12 h at −30° C. stored without stirring. Afterwards 8 ml of acetic acid and 140 ml of a 7% aqueous solution of tartratic acid is added and it is stirred for further 2 h at room temperature. After addition of 50 ml of a 20% aqueous solution of sodiumhydrogensulfit it is stirred for another 1 h and extracted with methylenchloride. The organic phase is dried by magnesium sulfate, evaporated and purified by chromatography on silica gel/Ethylacetate/heptane=1/3−>1/1. 6.3 g (74%) of product 3 is obtained in form of a light yellow solid compound: C40H47N3O7Si (709.92) MS (ESI+) 710 (M+H+).

Workup

  1. stirringwithout stirring
  2. stirringit is stirred for further 2 h at room temperature
  3. stirringis stirred for another 1 h
  4. extractionextracted with methylenchloride
  5. dry with materialThe organic phase is dried by magnesium sulfate
  6. customevaporated
  7. custompurified by chromatography on silica gel/Ethylacetate/heptane=1/3−>1/1

Sources & evidence

ORD record
ord-acc0ac9b6c7b4bea938c1bbd4ecf7787
Source dataset
uspto-grants-2008_10
Patent number
US07435727B2

Reaction notes

Loading…