Hydrochloric Acid → HCID 22467131, compound

HRID 1934737Notes

Reaction equation

HRID 1934737 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][CH:14]([CH3:33])[CH2:15][CH:16]=[C:17]1[CH2:32][CH2:31][C:20]2([S:24][CH2:23][C:22](=[O:25])[N:21]2[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:19][CH2:18]1.Br[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].Cl>CCCCCC.O1CCCC1.C(OCC)(=O)C>[C:39]([O:38][C:36](=[O:37])[CH2:35][CH:23]1[C:22](=[O:25])[N:21]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:20]2([CH2:31][CH2:32][C:17](=[CH:16][CH2:15][CH:14]([CH3:33])[CH3:13])[CH2:18][CH2:19]2)[S:24]1)([CH3:42])([CH3:41])[CH3:40]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 79177tert-Butyl bromoacetateHCID 224671633-[8-(3-Methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acidHCID 178418339Butyllithium

Product 1

HCID 22467131HCID 22467131, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

In an atmosphere of nitrogen, 1.97 ml of N,N-diisopropylamine was added to 10 ml of anhydrous tetrahydrofuran, to which was dropwise added 9.50 ml of a solution of n-butyllithium in hexane (1.58 mol/L) at −30° C. The mixture was stirred at the same temperature for 10 minutes and then cooled to −70° C., to which was dropwise added a solution of 1.56 g of 3-[8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acid in 20 ml of anhydrous tetrahydrofuran. After stirring the resulting mixture at the same temperature as above for 30 minutes, 0.89 ml of tert-butyl bromoacetate was dropwise added at the same temperature. After elevating the temperature to 0° C., the reaction mixture was poured into a mixture of ice water and ethyl acetate, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Thus, 2.23 g of 3-[2-[2-(tert-butoxy)-2-oxoethyl]-8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acid was obtained as a yellow oily product.

Workup

  1. customat −30° C
  2. additionwas dropwise added at the same temperature
  3. customto 0° C.
  4. customthe organic layer was separated
  5. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a543183556fc4db58b35f61a7a5b9e79
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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