Triethylamine → HCID 14919364, compound

HRID 867430Notes

Reaction equation

HRID 867430 reaction equation
[CH3:1][C:2]1([CH3:16])[S:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C@H:3]1[C:13]([OH:15])=[O:14].C(N(CC)CC)C.[Cl:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][C:30]([CH3:35])([CH3:34])[C:31](Cl)=[O:32])=[CH:27][CH:26]=1>ClCCl>[Cl:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][C:30]([CH3:34])([CH3:35])[C:31]([N:4]2[C@@H:3]([C:13]([OH:15])=[O:14])[C:2]([CH3:16])([CH3:1])[S:6][C@H:5]2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27813122-(4-Chlorophenoxy)-2-methylpropanoyl chlorideHCID 2825753HCID 2825753, compound

Product 1

HCID 14919364HCID 14919364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.17 g (5 mmoles) of 5,5-dimethyl-2-phenylthiazolidine-4(S)-carboxylic acid and 0.7 ml of triethylamine are dissolved in 20 ml of dichloromethane while stirring and the solution is cooled to 0° C. Then, 2-(4-chlorophenoxy)-isobutyryl chloride dissolved in 4 ml of dichloromethane is added under stirring. After stirring for 3 hours, the solution is washed with water, dried over anhydrous magnesium sulphate and evaporated. The obtained syrup is recrystallized from methanol by adding water to give the title compound in a yield of 1.39 g (64%), m.p.: 177°-181° C., [α]D21 =0° (c=0.94, dimethylsulphoxide).

Workup

  1. additionis added
  2. stirringunder stirring
  3. stirringAfter stirring for 3 hours
  4. washthe solution is washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. customThe obtained syrup is recrystallized from methanol
  8. additionby adding water

Sources & evidence

ORD record
ord-189b8daad2044f2c979e33538d8e5141
Source dataset
uspto-grants-1988_10
Patent number
US04775675

Reaction notes

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