Hydrochloric Acid → HCID 22467129, compound

HRID 1934756Notes

Reaction equation

HRID 1934756 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:15]1[C:19]2([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[S:18][CH:17]([CH2:25][C:26]([OH:28])=[O:27])[C:16]1=[O:29])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)([CH3:32])[CH3:31].Cl>C(Cl)Cl.C(N(CC)CC)C>[CH2:8]([N:15]1[C:19]2([CH2:20][CH2:21][N:22]([C:37](=[O:38])[C:36]3[CH:40]=[CH:41][C:33]([CH:30]([CH3:31])[CH3:32])=[CH:34][CH:35]=3)[CH2:23][CH2:24]2)[S:18][CH:17]([CH2:25][C:26]([OH:28])=[O:27])[C:16]1=[O:29])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 27594864-Isopropylbenzoyl chlorideHCID 22467162HCID 22467162, compound

Product 1

HCID 22467129HCID 22467129, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

In 5 ml of methylene chloride was suspended 0.25 g of 4-isopropylbenzoic acid. Then, at ambient temperature, 0.12 ml of thionyl chloride and 0.03 ml of N,N-dimethylformamide were added. After stirring the mixture at the same temperature as above for one hour, the solvent was distilled off under reduced pressure, and an azeotropic distillation treatment using toluene was carried out to obtain 0.25 g of 4-isopropylbenzoic acid chloride. To a suspension of 0.50 g of trifluoroacetic acid salt of 2-(4-benzyl-3-oxo-1-thia-4,8-diazaspiro[4.5]decan-2-yl]-acetic acid in 5 ml methylene chloride were successively added dropwise at 0-5° C. 0.64 ml of triethylamine and a solution of 0.25 g of 4-isopropylbenzoic acid chloride in 5 ml methylene chloride. The resulting mixture was stirred at ambient temperature for 24 hours. The reaction mixture was poured into ice water, pH was adjusted to 1.0 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. Purification of the residue by column chromatography [eluents: toluene:ethyl acetate=1:1, followed by chloroform] gave 0.30 g of 2-[4-benzyl-8-(4-isopropylbenzoyl)-3-oxo-1-thia-4,8-diazaspiro[4.5]-decan-2-yl]-acetic acid as a light yellow solid product.

Workup

  1. additionwere successively added dropwise at 0-5° C
  2. customthe organic layer was separated
  3. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customPurification of the residue by column chromatography [eluents: toluene:ethyl acetate=1:1, followed by chloroform]

Sources & evidence

ORD record
ord-7a35d4a16ffb4415a1fb9950aa41961a
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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