Hydrochloric Acid → (3S)-8-(3-methylbutylidene)-4-(4-methylpentanoyl)-1-thia-4-azaspiro[4.5]-decane-3-carboxylic acid

HRID 2249613Notes

Reaction equation

HRID 2249613 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][CH:4]=[C:5]1[CH2:17][CH2:16][C:8]2([S:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[NH:9]2)[CH2:7][CH2:6]1.C(N(CC)CC)C.[C:26](Cl)(=[O:32])[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30].Cl>C(Cl)Cl>[CH3:1][CH:2]([CH3:18])[CH2:3][CH:4]=[C:5]1[CH2:17][CH2:16][C:8]2([S:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[N:9]2[C:26](=[O:32])[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 170008Pentanoyl chloride, 4-methyl-HCID 68987170(3S)-8-(3-methylbutylidene)-1-thia-4-azaspiro[4.5]decane-3-carboxylic Acid

Product 1

HCID 57684379(3S)-8-(3-methylbutylidene)-4-(4-methylpentanoyl)-1-thia-4-azaspiro[4.5]-decane-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 8 ml of methylene chloride are dissolved 0.79 g of (3S)-8-(3-methylbutylidene)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid and 1.20 ml of triethylamine. Into the solution thus obtained are dropwise added a solution of isocaproyl chloride (prepared from 0.48 ml of isocaproic acid, 0.38 ml of oxalyl chloride and 5 ml of methylene chloride) in methylene chloride at 5-10° C., and stirred at ambient temperature for 2 hours. The whole was acidified to pH 2.0 with 2 mol/L HCl and extracted with CHCl3. The combined organic extracts were washed with water and brine, dried on MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography, [eluent; chloroform:methanol=9:1] to obtain 1.10 g of (3S)-8-(3-methylbutylidene)-4-(4-methylpentanoyl)-1-thia-4-azaspiro[4.5]-decane-3-carboxylic acid as a colorless crystalline product.

Workup

  1. customInto the solution thus obtained
  2. extractionextracted with CHCl3
  3. washThe combined organic extracts were washed with water and brine
  4. customdried on MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography, [eluent; chloroform:methanol=9:1]

Sources & evidence

ORD record
ord-fadef12ee2844f648509d30acee432d9
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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