Hydrochloric Acid → HCID 53880824, compound

HRID 1415678Notes

Reaction equation

HRID 1415678 reaction equation
C([Li])CCC.C[Si](C)(C)[NH:8][Si](C)(C)C.[C:15]([C:17]1[CH:37]=[CH:36][C:20]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1)#[N:16].Cl>C1COCC1>[C:15]([C:17]1[CH:37]=[CH:36][C:20]([C:21]([N:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:28]2)=[O:22])=[CH:19][CH:18]=1)(=[NH:8])[NH2:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 54097947HCID 54097947, compoundHCID 178418339Butyllithium

Product 1

HCID 53880824HCID 53880824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Li--N(Si(CH3)3)2 in 20 ml of THF, freshly prepared from C4H9Li and 1.13 g of hexamethyldisilazane, is added dropwise at -78°, with stirring, to a solution of 3.15 g of ethyl 3-(4-(4-cyanobenzoyl)piperazin-1-yl)propionate (FAB 316; obtainable by reacting 4-cyanobenzoyl chloride with ethyl piperazin-1-ylpropionate) in 50 ml of THF. The mixture is left to warm up to 20°, with stirring, aqueous hydrochloric acid is added, the mixture is washed with ethyl acetate, sodium hydroxide solution is added to pH 7.5 and the mixture is worked up in conventional manner and evaporated to give ethyl 3-(4-(4-amidinobenzoyl)piperazin-1-yl)propionate, FAB 333.

Workup

  1. additionis added dropwise at -78°
  2. waitThe mixture is left
  3. temperatureto warm up to 20°
  4. washthe mixture is washed with ethyl acetate, sodium hydroxide solution
  5. additionis added to pH 7.5
  6. customevaporated

Sources & evidence

ORD record
ord-44b892bb6bed4d089cb50d16b21b74e2
Source dataset
uspto-grants-1999_06
Patent number
US05908843

Reaction notes

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