Water → HCID 67917551, compound

HRID 1090205Notes

Reaction equation

HRID 1090205 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH3:18])=[C:8]2CO)=[CH:4][CH:3]=1.C[Si](C)(C)N[Si](C)(C)C.[K].[OH2:33].CN([CH:37]=[O:38])C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH3:18])=[CH:8]2)=[CH:4][CH:3]=1.[CH3:12][O:16][CH2:17][C:37]([OH:38])=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 15678806HCID 15678806, compoundHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt

Product 1

HCID 67917551HCID 67917551, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product from Step 2 above (1.0 g) was dissolved in dry DMF (10 ml) at -20° C. Potassium hexamethyl disilazane base in toluene (0.69M) was added (1.1 molar equivalents) and the reaction stirred for 1 hr. Ethyl 2-bromo acetate (580 mg)=1.2 equivalents was added and the reaction stirred for 16 h at 21° C. Water was added (3 ml). The product was isolated after extraction from the aqueous DMF with ether. Following purification on column chromatography, the title ethyl ester was hydrolysed in 3N NaOH according to the procedure in Example 2.

Workup

  1. stirringthe reaction stirred for 16 h at 21° C
  2. customThe product was isolated
  3. extractionafter extraction from the aqueous DMF with ether
  4. custompurification on column chromatography

Sources & evidence

ORD record
ord-5a2de98798494ea9a5a5580629d58ff9
Source dataset
uspto-grants-1992_01
Patent number
US05081145

Reaction notes

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